weekend trips to boston

A Perfect Weekend in Boston | Itinerary + Guide

By: Author Emily

Posted on Last updated: September 26, 2023

Up until recently, Boston was my favorite city that I’d never been to. Before I ever stepped foot in the city, I just had a feeling I’d love it there. We recently went to Boston for a long weekend, and I was pleased to have my suspicions confirmed. I loved it. If you too want to make your Boston dreams a reality, this is the post for you.

Follow along as we plan a perfect weekend trip to Boston, Massachusetts.

In This Post

• Getting to and Getting Around Boston

Where to Stay in Boston

• When to Go to Boston & How Long to Stay

Boston Weekend Itinerary

• Boston Walking Routes & Map

Other Things to do in Boston

How to get to boston.

If you’re coming from the Northeast, the train is a great option. We take Amtrak often and find that it’s usually on time and often very convenient. Amtrak has three routes with daily service to Boston.

• Northeast Regional: This train runs between Boston and Virginia. It makes stops in New Haven, New York City, Philadelphia, Washington DC, and many other cities along the way. The route separates near Alexandria and goes toward Roanoke or Norfolk.
• Acela: This train runs between Boston and Washington DC. It is a nicer train with Business and First Class only. It’s also a little faster and makes fewer stops than the Northeast Regional.
• Downeaster: This train runs between Boston and Brunswick, ME, stopping at 10 cities along the coast in between.

There are three Amtrak stations in Boston. The Northeast Regional and Acela trains stop at both South Station and Back Bay. South Station is the start of the line. If you’re traveling with a group in Coach on the Northeast Regional, I’d recommend traveling out of South Station. Since Coach is open seating, this gives you the best chance at finding seats together. The Downeaster trains stop at the North Station.

If you’re regional but not on a train line, driving is also an option. Boston isn’t the worst city to have a car. However, parking is expensive and not always available and/or complimentary at all hotels.

And finally, you can fly into Boston Logan International Airport if you’re coming from further away. There is no Metro station at the airport. Instead, there are frequent buses that run between the terminals and the Blue Line station. Even with the connection, this might still be the fastest option. Traffic around Boston Logan can be brutal.

Getting Around Boston

Boston has a decent Metro system that comprises both trains and trams, plus a wider web of bus routes. We found the trains and trams ran pretty frequently, but they didn’t have many cars and were often very crowded.

The Boston Metro does not have tap-to-pay gates. To board, you need to first purchase a ticket or transit card before you board. There are ticket kiosks at all stations. You can buy a one-way fare, load money onto a transit card (CharlieCard) or purchase an unlimited ride pass (CharlieTicket). Buses in Boston accept all of those ticket types, plus cash.

Central Boston is also pretty small (Fenway to the North End is only 3 miles). If you’re willing and able to walk, you can cover a lot of ground on foot. In fact, we often found that the Metro took just about as long as walking. The streets in Central Boston are a bit windy — we definitely missed Chicago’s grid system a few times. That makes them tricky to navigate, but it also means you can take slightly different routes each time.

The first thing to know when it comes to hotels in Boston is that they are expensive — and some are really expensive. Regardless of the season or day, it’s tough to find a hotel room for under $200 a night. Most hotels are going to be closer to the $250-$300 a night mark, with luxury hotels easily double that.

So once you’ve swallowed that pill, it’s time to pick your poison. Here’s a look at the best neighborhoods to stay in Boston and what hotels we recommend in each.

• Downtown: This is the business district, which is centrally located between Boston Common and the North End. It has the highest concentration of hotels. It’s busy during the week and pretty quiet on the weekend. We recommend The Langham (luxury) and Hyatt Centric Faneuil Hall (midrange).
• Back Bay: This upscale neighborhood is bustling all the time, particularly on nights and weekends. It has a great food scene and lots of shops nearby. It’s easily walkable to Fenway and Public Garden/Boston Common. We recommend The Lenox (luxury) and Courtyard Marriott Copley Square (midrange)
• Beacon Hill: This little pocket of town is charming as can be, but it’s a bit of a Metro desert. It’s not the best location for getting around to the rest of Boston. Stay here on your second visit when you plan to cozy up in Beacon Hill your whole stay. We recommend The Whitney Hotel (luxury) and Beacon Hill Hotel (midrange).
• Seaport: For a nautical New England vibe, head to this waterfront area on the south side of town. It is a bit trendier, has a lot of great views, and is close to its own set of activities. We recommend The Envoy Hotel, Autograph Collection (luxury) and Hyatt Place Seaport District (midrange).
• Fenway-Kenmroe: This is the area around Fenway Park. It is obviously a good pick if you’re just in town for a Red Sox game. There’s plenty of good restaurants and great parks nearby, too. We recommend The Verb Hotel or Residence Inn Back Bay/Fenway (both usually midrange, but expensive on game days).

We personally stayed in Downtown Boston at The Langham. The hotel was great, and it was a perfect location for our plans. The only thing we didn’t love was that several of the restaurants in the area were closed on weekends. Next time, I think we’d like to stay in Back Bay.

When to go to Boston

There’s a lot to consider when it comes to picking the best time to visit Boston.

First, there’s the weather. Boston has four distinct seasons with warm summers, cold winters, and consistent precipitation throughout the year. If you’re planning a lot of outdoor activities (like the Freedom Trail and parks), this matters a lot. We walked the Freedom Train when it was 85°F and sunny, and it was not fun. I assume it’s also not fun at 20°F.

The seasons also impact how the city looks and the activities that are available. In the fall, you might want to spend all of your time leaf peeping, taking colorful strolls through Public Garden and the esplanade. Christmastime will mean festive storefronts on Newbury Streets, Beacon Hill homes draped in garland and ice skating in Boston Common.

You also should plan for the specific things you want to do. Check the Red Sox schedule if you want to guarantee a game at Fenway. If you want to stay at a boutique hotel (like the Newbury Guesthouse), be sure to check their availability. Boston also has a handful of festivals you might want to plan around, like the Boston Seafood Festival in September or St. Anthony’s Feast in the North End in August.

Finally, think about the day(s) of the week you’ll be visiting and how that impacts your plans. For example, the business district downtown can be pretty dead on weekends and many restaurants are closed. If you do the Freedom Trail on a Sunday morning, you might not be able to go inside the churches. Tours of the Massachusetts State House are only available Monday – Friday.

So when is the best time to go to Boston? Personally, I’d recommend late spring (May-June) if you want to see a Red Sox game or peak fall (October) if you don’t care about baseball.

A visit to Fenway can really anchor a trip and is absolutely worth planning around. Late spring/early summer will give you the best shot at a game with good weather. Fall in Boston looks like an absolute dream. I planned a fall trip that we had to cancel last minute. Now that I’ve seen Boston in the summer, I’m even more confident that Boston in the fall would be perfect.

I would avoid summer if you are interested in the Freedom Trial, because the long outdoor walks are no fun in the heat. Christmas in Boston looks lovely, but any chance of snow can make travel plans flimsy and stressful. So for that reason, I’d avoid winter too.

How Long to Stay in Boston

A long weekend in Boston is pretty perfect. Ideally, you want to have at least two full days. If you have an extra half day on either of your travel days, that’s even better. That will give you just enough time to get a taste of the city and check off some of your must-dos. You won’t have time to do it all, but it’s a good excuse to plan another trip during a different season.

If this is your only trip to Boston in the foreseeable future and you want to get the most out of it, I’d suggest giving yourself at least 4 full days. With that much time, you could easily spend a day on the Freedom Trail, explore several different neighborhoods, make it to a Red Sox game (if in town) and visit a few museums.

In these next few sections, we’ll walk through our Boston weekend itinerary. We’ll narrate our specific experience, while also providing tips and recommendations based on what we learned. Before we get into the specifics, here are a few things to note about this itinerary.

We traveled from New York City to Boston on a Friday morning and left Monday morning. That gave us 2.5 days to explore the city. We were traveling with an almost-3-year-old, so our schedule includes nap times (most days) and early bed times. Our trip was in mid-July in the middle of a record heat wave and the Red Sox were in town. We stayed Downtown at The Langham.

And a final disclaimer, this itinerary calls for quite a bit of walking. Boston does have a Metro, but it didn’t always connect the places we needed to go. In many cases, the Metro was only a few minutes faster than walking, so we chose to walk.

Our NYC toddler is a great walker, so this worked out for us. If you are traveling with a child who can’t walk that far, be sure to bring a baby carrier or stroller. Strollers are generally fine around most of Boston, but they won’t fare as well on the cobble stones of Beacon Hill or the narrow sidewalks of Newberry Street. Instead, we highly recommend baby wearing for trips like this .

Without any further ado, let’s get this itinerary!

Arrival Day – Back Bay

We arrived in Boston by train around 1 PM and then made a quick 10-minute walk to our hotel (The Langham, Downtown Boston.) We checked in and our room was ready. They immediately sent housekeeping to our room to make up the sofa bed, so our toddler was napping shortly before 2 PM.

With a good 2-hour nap under our belt, we set off for Back Bay. We took the Green Line Metro (C or D lines work) to Hynes Convention Center Station, ready to walk Newbury Street from west to east.

Back Bay is a high-end shopping and dining district with several residential streets and office buildings mixed in. It’s a charming neighborhood with rows of brownstone homes, which give the area it’s distinctive look.

The heart of Back Bay is Newbury Street between Massachusetts Ave and Public Garden. The west end has more affordable shopping and the highest concentration of restaurants and the east end has the designer shopping.

I absolutely loved Back Bay. Unfortunately, our toddler was being a bit of a terror that day. (What is it about travel days that just turns children into gremlins?) We didn’t get to spend nearly as much time here as I would have liked, so it will definitely be on my itinerary next time we visit.

Things to see & do in Back Bay

• Newbury Comics: Their comic collection actually leaves much to be desired, but they have some great apparel, toys and gift-y items.
• Trident Booksellers & Cafe: Lovely bookstore, but I don’t recommend eating here when there are countless better options just down the street.
• Boston Public Library: This historical public library is free and open to the public. It’s a beautiful building that’s worth visiting even without a library card.
• Emack & Bolio’s : Yes, this is a chain, but it originated not far away in Brookline, MA so it still feels a bit local. It’s also delicious.
• Dirty Water Dough Company : Easy dinner option with outdoor seating and clever pizza combinations (including a vegan option).
• Buttermilk & Bourbon: Higher end dining option for southern food and seafood.
• Clarendon Street Playground: If you have kids, this is a good detour.
• Copley Square & Trinity Church : This entire area was under construction in summer 2023, but it’s worth noting for a future visit. Old South Church is also over here and very pretty.
• Commonwealth Ave Mall: If you’re making a loop through Back Bay, walk one direction down Newbury Street and the other down the mall. This walk would be extra pretty in the fall.
• Charles River Esplanade : This narrow park along the water has paved paths for running or walking, a playground, kayaking in the lagoon, and more. Great views, too.

Newbury Street ends at Public Garden, which borders Boston Common. Though not actually a part of Back Bay, these parks are a great place to relax before or after a stroll down Newbury Street. We walked through both on our way back to our hotel.

Day 1: Beacon Hill & Fenway

If you had one day in Boston, I would follow this itinerary to a T (plus maybe add a few things during the time we spent napping.) We strolled through the cutest neighborhood in town, explored a waterfront park, and then spent the evening at one of the most beloved baseball stadiums in the MLB.

Here’s how we spent our first full day in Boston.

Coffee & Breakfast at Tatte

Tatte (pronounced like “latte”) is a bakery and coffee shop chain in Massachusetts and Washington, DC. There are many locations in Boston, including in Beacon Hill. We personally went to the location closer to our hotel before heading to Beacon Hill, but you could do it either way.

What I love about Tatte is that you can just stop in for a quick coffee and pastry to go, or you can order a full restaurant-quality meal to eat there. It was the perfect place to enjoy a delicious breakfast without spending quite as much time as we would at a table-service restaurant.

The food was incredible. I had the most delicious halloumi breakfast sandwich, Kenny had the sweet french toast, and our toddler got the pancakes with the toppings on the side. The pancake order came with three giant pancakes, so we took two to our hotel and had breakfast for the next two days.

A Walk Through Beacon Hill

We walked from Downtown to Beacon Hill via Beacon Street to Joy Street to Mt. Vernon Street and on over to Charles Street. Taking a winding path through Beacon Hill is highly recommended.

I said Back Bay was charming, but Beacon Hill is somehow even cuter. Beacon Hill is exactly what I pictured Boston to be and it was perfect in every way. (It reminded me a lot of Gold Coast in Chicago, if you’ve been there.)

The neighborhood is one of the oldest in Boston and is largely residential. The streets (some of which are cobble stone) are windy and hilly, lined with federal style row houses and street lights that glow with real flames. The main shopping street — Charles Street — runs along the west side of the neighborhood and has a lovely collection of local shops and stores that feel so quintessentially New England.

Here are my favorite spots in Beacon Hill:

• Beacon Hill Cafe & Books: This book shop is great for people of all ages, but the kids section on the top floor is absolute perfection. There’s a little kid-sized door, a train that runs around the rooms, and lots of little chairs for your little reader. The cafe looks incredible, but reservations book up quickly, so we didn’t get the chance to try it.
• Gus & Ruby Letterpress: I love a card shop, and this one is perfect. They have cards, but also a great selection of little gifts, party supplies, colorful pens, etc.
• Whitney + Winston: If you have little ones in your life, you have to stop here. They have the most adorable clothes (pricey, though) and unique toys (my toddler was in love with the wooden barista set).
• East Coast Ivy Boutique: Don’t worry, adults have cute boutiques on Charles Street, too. The only thing people love more than the curated style is the kind salespeople.
• Mt. Vernon Street: This street is one of the most lovely in Beacon Hill, but honestly it’s worth strolling around all the residential streets over here. There are two other popular streets (Acorn Street and Louisburg Square), that are very beautiful but have signs that they’re private to residents. If you choose to venture down those streets, please be respectful.
• Blank Street Coffee: This is a chain coffee shop that’s all over, but I’ll take it over Starbucks any day. They have the best seasonal specialty drinks that always set the mood.

Charles River Esplanade

There’s a pedestrian bridge that connects Beacon Hill to the Charles River Esplanade. The esplanade is a large park along the banks of the Charles River that is cut in half by a narrow lagoon.

There are paved pathways around the entire park, so it’s popular with runners, bikers, and stroller parents. You can watch the boats sail past on the river side of the park or kayakers in the lagoon on the land side. There’s a playground and baseball diamond on the north end of the park, a small outdoor amphitheater, seasonal beer garden, and a splattering of monuments. The Charles River Esplanade also has several public bathrooms, which were clean in our experience.

We came to the esplanade for the playground. After a morning shopping in Beacon Hill, our toddler was due for some running around. The playground over here was nice, but it’s definitely targeted to bigger kids. (My kid is almost 3 and needed help with most things.) There was one big slide, but it was broken (it had a small hole on the side and was blocked off with a cone). The only way to get to the top of the slide was by climbing a web of nets, which wasn’t easy. There was also several spinning apparatus and a zip line.

The Charles River Esplanade was nice in the summer, but it looks like it would be extra lovely in the fall. Honestly, all of Boston looks like it would be lovely in the fall. (Okay, but also aren’t all places better in the fall? I digress.)

Lunch at Clover Food Lab

It was noon by the time we left the park and we were starving. We walked back toward downtown to get lunch because it was on the way to our hotel. There are lots of good options around here, but we chose Clover Food Lab.

Clover Food Lab is a quick-service vegetarian restaurant with several locations in Boston. It’s a good pick for vegetarians and/or coffee snobs. They have seasonal plant-based sandwiches, bowls and plates that are a nice and healthy alternative to the Impossible burger, salad or pasta option that typically checks the vegetarian box at most restaurants. Plus they have a curated coffee menu brewed primarily via pourover.

We walked from the Charles River Esplanade to the Clover Food Lab on School Street (near the Old Corner Bookstore on the Freedom Trail). It wasn’t a short walk walk (0.9 miles), but Google Maps said taking the Metro would only save us one minute. We were fine to enjoy the walk, most of which was through Public Garden and Boston Common.

We ordered the BBQ seitan sandwich, Impossible meatball sub and the peanut better/banana/honey sandwich for our kiddo. It was a bit expensive for what it was, but everything tasted delicious. We also got a blueberry lemonade and hibiscus tea, which were incredibly refreshing in the summer heat.

Our toddler can make it all day without a nap, but it’s not ideal. We only like to skip naps when we have to (which we’d end up doing the next day), and choose to take a nap break at the hotel today. I’d be lying if I said I didn’t also appreciate the 2-hour AC break in the middle of a long day.

My husband put our kid down for the nap and then went for a run in the hotel fitness center. I laid on the floor watching cooking shows on my phone and falling in and out of sleep. Same, same.

Red Sox Game at Fenway Park

We knew we wanted to plan our trip to Boston around a Red Sox game. As luck would have it, the New York Mets were playing at Fenway during one of the free weekends we had this summer. (We line in Queens and are Mets fans.) We happily planned our Boston trip around that.

The game was originally scheduled for 4 PM (pretty much perfect for our toddler who naps 1-3), but due to a rain delay it was pushed back to 7 PM (much less perfect for a toddler who goes to bed at 7.) We briefly considered skipping it, but decided it was worth a shot. We figured there was probably enough ice cream and popcorn to keep our kid distracted from the late bedtime.

It turned out okay and the game was absolutely incredible. As former Chicago locals who spent a lot of time at Wrigley Field, we were thrilled to get back to a real historical baseball field. The park was great and everyone was surprisingly nice to us — from the Red Sox dads behind us to the Mets fan next to us to the Fenway staff member who averted a near total meltdown by replacing our spilled popcorn.

We spent way too much money on good seats, but it was worth it. Our toddler could actually see the ball and the game being played, which kept them interested longer. Plus we had seats that were the front corner of a section, so our toddler could be trusted to sit or stand in their seat space without us worrying about them bothering fans next to or in front of them. It was truly a magical evening of baseball.

I have a detailed First Timer’s Guide to Fenway Park , but there are two things I will say in this post.

2 things to know about Fenway

• Get there early — like early, early. The gates open 90 minutes before the game, but crowds get there much sooner. We left at 4 PM for a 7 PM game and we had very little down time. After navigating the crowds on the Metro and at the stadium, taking a walk through the ballpark, and getting food, we were barely at our seats by game time.
• The Metro after the game is awful . The Green Line that stops near Fenway at Kenmore is not a proper metro train. It’s a tram with 2 cars. That is not enough for a stadium full of people. Plus, they didn’t seem to increase service to account for the crowds. It took forever, it was packed, and it was extremely unpleasant. (That’s coming from people who frequently crammed onto Red Line trains after Cubs games. It’s way worse than that.) Depending on how you feel about that, you will want to skip it entirely, leave before the game ends, or just be mentally prepared for it to suck.

Day 2 — The Freedom Trail

The Freedom Trail is a literal brick trail that leads past a series of historical sites around Boston. In full, the Freedom Trail is about 2.5 miles long and passes 16 sites. Most of the Freedom Trail is in the Downtown and North End neighborhoods, with the final few stops across the river in Charlestown.

If you want to visit all of the sites on the trail, go inside the sites that allow it, stop for meals, etc, the Freedom Trail will take an entire day. And even still, you might be hard-pressed to do it all and still make it to the final attraction (Bunker Hill Monument) before the inside portion closes at 4:30 PM. Doing the entire Freedom Trail in a single day is pretty exhausting.

Alternatively, we recommend a shortened version of the Freedom Trail. You can spend a half day on the Freedom Trail and finish up at Faneuil Hall for lunch. Another good options is to add a few more stops and finish at Old North Church in time for dinner in the North End. If you’re interested in the details of a shortened route, be sure to check out our Boston Freedom Trail in a Day | Guide + Map post.

If you take a shortened route that ends at either Faneuil Hall or Old North Church, you have more flexibility in your schedule to add in some unofficial Freedom Trail stops. The Sam Adams Taproom, Mike’s Pastry or even just a leisurely lunch somewhere are all great options that you might not otherwise have time for.

I wouldn’t feel bad missing the final few stops. The walk there is long and boring, and I would argue that these final two sites feel disjointed from the rest of the trail. If you do really want to see these final sites, I would do it on a different day. Not only will you have more time and energy to enjoy them (the Naval Yard alone can fill an entire morning), but you also won’t have to rush through everything else to get there.

But hindsight is 20/20. Here’s how we actually spent a full day on the Freedom Trail.

Freedom Trail (and more!) Walking Route & Timeline

Note: The (*) indicates stops that were along the trail, but not technically part of it.

• Boston Common (10:15 AM): We spent a half hour here, which included a stop at the playground and the small visitor center.
• Massachusetts State House (10:45 AM ): Tours are available, but we did not go inside.
• Park Street Church ( 10:50 AM ): We took a quick lap through the church, which has seen one too many restorations to be interesting.
• Granary Burying Ground (10:55 AM): We were offered a complimentary map which pointed us to the main grave sites. The large tour groups made this stop pretty awful.
• King’s Chapel (11:05 AM): You can usually go inside this church, but we caught it on a Sunday morning when it was closed to the public for service.
• Boston Latin School & Ben Franklin Statue (11:15 AM): The school is really just a mosaic monument and the statue is a statue. Quick and uneventful stop.
• Old Corner Bookstore (11:20 AM): The building still stands, but it’s no longer a bookstore. In fact, it’s a Chipotle restaurant. Another quick stop.
• Lunch break* (11:25 AM): We ate at said Chipotle and it was the worst Chipotle I’ve ever been to in my entire life. Just atrocious service, dirty store, and poorly made food. 0 out 10 recommend. Eat anywhere else in Boston.
• Old South Meeting House (12 PM): We bought a combo ticket to go inside this building and the next. The Old South Meeting House is one large room with a small museum exhibit along one side. They did have good, clean bathrooms downstairs.
• Old State House (12:15 PM): We used our joint ticket to go inside here, too. The museum portion was much bigger and well done, plus there was a gift shop (free to enter) and more clean bathrooms.
• Boston Massacre Site (12:30 PM): This is just a marker on the ground. Quick visit.
• Sam Adams Tap Room* (12:35 PM): We took a much needed break and enjoyed a beer (and a root beer) on the rooftop patio. The taproom is huge and the location across from Faneuil Hall is perfect. 10/10 recommend adding this to your route.
• Faneuil Hall (1:15 PM): This stop could take 5 minutes or 5 hours. There is Faneuil Hall Visitor Center which is mostly souvenir shops and then there is Faneuil Hall Marketplace which is massive and has a variety of restaurants and stores in and around it. We breezed through most of this, but would come back again.
• Paul Revere House (1:45 PM): I would have liked to go inside here, but the line was too long we were too hot and tired to wait in it. You can’t see much from the outside, so this was quick.
• Mike’s Pastry* (1:50 PM): This is a North End institution, so I was happy to wait the 20 minutes in line for a cannoli and slice of Boston creme pie. We ate our treats in the park by the Paul Revere Statue, which seemed to be the unofficial Mike’s Pastry seating area.
• Old North Church (2:40 PM): While Kenny got us some afternoon iced coffee, I took our toddler into the church. It was a $5 adult ticket, and kids 5 and under were free. The church itself was just okay, but they had a scavenger hunt for kids which mine loved . They got a sticker at the end for finishing it, and it was probably the highlight of the trip for them.
• Copp’s Hill Burying Ground (3:05 PM): We didn’t recognize any of the names of people buried here. We were so hot and tired by now that we just poked our heads in and carried on.
• USS Constitution (3:30 PM): We got to the Charlestown Naval Yard at 3:30 and immediately cooled off in the visitor center for a bit. The ship itself is free and was really cool, but we were just over it by now. You can also board the USS Cassin Young for free, which I popped into quickly while Kenny & Zoe relaxed in the shade. There’s also a museum, which we didn’t have time for.
• Bunker Hill Monument (4:40 PM): It was a hike to get here and a hike to get back to the train after and it wasn’t worth it. We didn’t want to go to the top, but it was closed even if we did.

After Bunker Hill, we walked 0.6 miles to the Orange Line stop at Community College Station. We took the train downtown and went back to our hotel. Instead of going out for dinner, we decided to go for a swim at the hotel pool and order room service.

If I sounded grumpy at the end, it’s because I was. It was just a really hot, really long day. The final stops just were not worth it for us. Looking back, we wish we would have just called it early and had dinner in the North End after the church.

Departure Day

Our train back to New York City departed South Station at 9:15 AM. We had a quick breakfast in our room and then walked to the station.

The Northeast Regional train starts in Boston at the South Station and then makes its first stop at the Back Bay station. Even if your hotel is closer to Back Bay, I’d still recommend traveling out of the South Station. This Amtrak train is open seating, so if you board at Back Bay, you might have a hard time finding seats together on a full train.

Otherwise, the train was very pleasant. It wasn’t quite as nice or as fast as the Acela, which we took too Boston, but it wasn’t bad. We snagged three seats in one of the few quads on the train, and it was perfect. (Oh! Also watch out for the Quiet Car, which is the second from the rear after the Business Class car. We accidentally sat there and had to move because our toddler definitely could not maintain a “library like atmosphere.”)

Boston Itinerary Walking Map

All of the walking routes in the itinerary above have been plotted out on the map below.

Before you dive in, here are a few quick tips for using this map.

• To view the map in Google Maps, click the expand icon on the top right corner.
• Click the star icon to save the map to your Google account for later. To access the map again, open Google Maps > click the Saved tab > click Maps.
• You can click the checkboxes beside each day’s walking route to add or remove those items from the map. This will help you see the map for one day at a time.

We easily filled 2.5 days in Boston, but left with a long list of things we still wanted to do. Here’s a peak at some other things to do in Boston that we didn’t cover here.

• Swan Boats at Public Garden: For under $5 a person, you can take a ride around the pond at Public Garden aboard the iconic swan boats. Boats run from mid-April to early September from 10 AM to 4 or 5 PM (varies by date).
• Boston Tea Party Ships & Museum : If you’re in Boston for history, this is probably a must-do for you. Tickets are pricy ($38 general admission) but include a 1-hour guided and interactive group tour.
• Boston Children’s Museum / Museum of Science: Both of these museums are good if you have kids and/or if the weather is bad.
• Eating & Drinking in the North End : The North End is Boston’s Little Italy. It’s filled with restaurants, bakeries and bars that are as tasty as they are historic. It’s a perfect place to end up after a Freedom Trail half day.
• Christopher Columbus Waterfront Park: We hardly saw the water at all during our Boston trip, and that’s wild to me! This park is beautiful and really gives New England harbor vibes.
• Back Bay Fens & Arnold Arboretum: If you’re visiting in the spring or fall and want to spend more time outside, both of these parks look stunning.
• Trillium Brewing Company: Drinking and Boston go hand in hand. If you’ve already checked off the Sam Adams Taproom and an Irish Pub, a brewery is next. Trillium is one of the best in Boston.
• Day trip to Salem, MA: It’s a quick 30 minute train ride to get from Boston to Salem. Most famously known for the Witch Trials and Hocus Pocus, this small town celebrates Halloween all year long (but mostly all of October.)

Closing Thoughts

I absolutely loved Boston. It had the conveniences of major city with the charm and walkability of a smaller New England town. (She says having been to no other New England towns). I loved exploring each of the different neighborhoods and re-learning a lot of the history. If you eat seafood, I can imagine you’d love Boston even more.

While Boston has a lot more to see and do, it’s still a great weekend destination for East Coast travelers. It’s easy to get to from around the region, which makes it appealing for repeat visits. We enjoyed our summer trip and going to Fenway, but I will absolutely prioritize fall for our next visit.

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Boston Itinerary: A Weekend Trip To Boston, MA

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On a Boston weekend trip, visitors have an array of options regarding how to spend their time. In our Boston Itinerary, we feature a range of activities so that travelers can get a taste of all the city has to offer!

Weekend Trip to Boston Itinerary

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We highlight top Boston attractions and intriguing neighborhoods – as well as historic places and iconic eateries. Our detailed itinerary for a Boston getaway weekend is all you need to plan your trip!

3 Days in Boston

The first question many travelers ask is, How many days in Boston for a trip? For our weekend getaway, we outline the best way to see Boston in 3 days. We believe visitors can squeeze the top things to do in Boston into a well planned 3 day trip.

Our 3-Day Itinerary assumes that you will spend a long weekend in Boston, arriving early on Friday or Saturday and staying until Sunday or Monday evening. However, as not all Boston vacations take place over the weekend, our trip plan can also be used for weekday visits.

Furthermore, we understand that not everyone is planning 3 days for Boston weekends. Some people are limited to visiting Boston in a day, while others are trying to plan a 5-Day Boston getaway. To help fellow travelers, we outline several sample itineraries with top tips on how to plan a trip to Boston for any timeframe! 

Planning a Weekend in Boston Itinerary

When we recently visited for a long weekend in Boston, it wasn’t our first trip to the city. Far from it, actually. Our previous Boston weekend trips had revolved around sporting events (admittedly, one of the best things to do in Boston), but we had missed out on some of the top sights.

On this weekend trip, we arrived with plans; big plans to see the Best of Boston! We were ready to spend a weekend in Boston that included visiting historic points of interest, exploring great neighborhoods and dining on local fare.

Armed with this detailed plan, we were ecstatic to finally have a complete Boston 3-Day Itinerary. Now, we are sharing those details to help you create your perfect weekend Boston trip plan!

Pro Tip:  Get (and stay) organized for your Boston Trip by using our Travel Planning Printables !

3-DAY BOSTON ITINERARY

Our Boston long weekend trip plan includes absolutely everything you need to know for visiting Boston in 3 days. In addition to our day-by-day Boston guide, we include tips for how to get there, where to stay and what to pack.

Save, Pin or Bookmark our Boston Travel Guide to plan your trip to New England!

Day 1: Freedom Trail, Famous Landmarks and Fenway Park

Day 1 of your Boston Weekend Itinerary is all about historic spots, local eats, lush parks and the Red Sox! After getting situated in your accommodations (suggestions below), start your trip by visiting top Boston sights and taking in a baseball game at famous Fenway Park.

Freedom Trail Boston

Walking the 2.5-mile Freedom Trail is a must-do activity on weekend trips to Boston. The full route includes 16 of Boston’s top historic sites – all of which played a role in shaping the future of the Untied States of America. 

Sights on the Boston Freedom Trail

The Freedom Trail sights are listed in order so that you end in Boston Common and then continue on from there.

Technically, this is considered walking the trail backwards, but we believe that it makes more sense to complete the route in reverse. The order of the stops doesn’t actually matter. In fact, you can pick and choose which sights you want to see if you have other interests for things to see in Boston in three days. 

Freedom Trail Route and Sights

Our recommendations is to begin your Freedom Trail Walk in Boston at Bunker Hill. 

• Bunker Hill – An obelisk monument marking the first battle of the Revolutionary War; visitors can climb up the tower and visit the nearby museum. 
• USS Constitution Museum  – Nicknamed Old Ironsides, it is the oldest US warship still floating.
• Copp’s Hill Burying Ground – Historic cemetery for North End residents.
• Old North Church and Paul Revere Statue – Boston’s oldest church, which is most well-known for it’s part in the start of the American Revolution – One if by land, two if by sea.
• Paul Revere House – The home where Paul Revere lived in the late 1700s.
• Faneuil Hall – The site of America’s first ‘Town Hall Meeting’ and a place where many events of the American Revolution occurred. 
• Boston Massacre Site – The site of the clash between residents and Redcoats in March 1770. 
• Old State House – The oldest public building in Boston (circa 1713).
• Old South Meeting House – The site of countless meetings and speeches that led to the events of the Boston Tea Party; now a museum. 
• Old Corner Bookstore – Built in 1718; it ranks as the oldest commercial building in Boston.
• Ben Franklin Statue and Boston Latin School – The oldest public school in the United States, established in 1635, which was attended by Benjamin Franklin.
• King’s Chapel and Burying Ground – An Anglican church (Boston’s first) dating to 1686.
• Granary Burying Ground – Cemetery dating to 1660 where many famous residents – such as John Hancock, Samuel Adams and Paul Revere – are buried.
• Park Street Church – Founded in 1809, the steeple rises 217 feet; it was one of the tallest structures in Boston when it was built. 
• Massachusetts State House – Gold-domed building housing Massachusetts government since 1798.
• Boston Common – The city’s first (and best!) green space.

Freedom Trail Tour or Self-Guided Walk for your Weekend in Boston?

On your long weekend Boston trip, you will need to decide if you want to join a guided walking tour or complete the Freedom Trail on your own. There are pros and cons to both.

Guided Tour of Boston

An engaging guided tour – like this one – features a local who will provide facts about the history of Boston. Best of all, they will lead the way. However, you will be on the guide’s timetable and will likely not have the opportunity to go inside some of the sights. 

Boston Self-Guided Walk

Visitors can also opt to do a Self-Guided Freedom Trail Walk. The route is fairly easy to follow – as it is marked by a red stripe through the streets of Boston. Plus, all 16 Freedom Trail destinations include informational plaques. For more interesting facts along the way, you can download an audio guide . 

Those exploring on their own will be able to enter sites along the way and make a few detours to other nearby Boston points of interest. Expect the walk to last at least 2 hours, but it could take longer depending on your curiosity, pace and detours. We recommend getting an early start and finishing the trail by mid-afternoon.

Pro Tip: If you choose to complete the route in the opposite direction, just make your way back to Boston Common using the subway (just called the T). Either the Green or Orange line will get you there! 

Lunch on the Freedom Trail

There are plenty of places to stop to eat along the Freedom Trail, however we have a few suggestions. All of our recommended Boston restaurants for lunch are in the North End neighborhood along the Freedom Trail route. 

Quincy Market

Faneuil Hall is an official stop on the historical Freedom Trail. Part of a complex of buildings called Faneuil Hall Marketplace, it also includes the Quincy Market. The historic Boston marketplace dates to the mid-1800s and today it is packed with many famous eateries.

The Bell in Hand Tavern

We love the classic pubs in Boston – and The Bell in Hand Tavern is one of the best! Located along the Freedom Trail (but not an official stop), The Bell in Hand Tavern claims to be the oldest tavern in America. 

Lobster Rolls

If you are looking for a scrumptious seafood lunch, then a Boston ‘Lobstah’ Roll is the way to go! These two restaurants in Boston are well-known for their Lobster Rolls: Neptune Oyster in the North End and Union Oyster House in downtown.

Boston Public Market  

An upscale, indoor market, Boston Public Market features 30 local vendors, including numerous chic eateries. The market is across the street from The Bell in Hand. 

Boston Common and Public Garden

Anyone visiting Boston in a weekend will want to spend some time on the Common. Established in 1634, it’s the oldest park in the USA. Stroll through the space from east to west, passing by the popular Frog Pond and walk into Public Garden. 

Boston Public Gardens is a botanical garden (the first in America) and opened in 1838. The two most popular sights are the Swan Boats and the Make Way for Ducklings statue. It is highly recommended that you include paddling a Swan Boat to your Boston trip planner!

Back Bay Boston

Built on reclaimed land along the marshy banks of the Charles River, the affluent Back Bay neighborhood features wide, tree-lined boulevards and Victorian Brownstones. However, Back Bay also thrives as a commercial hub and one of the top shopping destinations in Boston. The district is a must-see when you visit Boston for the weekend.

At the heart of the district is Copley Square, which is where the famed Boston Public Library stands. Other significant Back Bay structures include 200 Clarendon Street (formerly the John Hancock Tower), Trinity Church and the Prudential Tower.

Pro Tip : Get an overview of the Freedom Trail and Back Bay on a 2-hour guided tour of the area. This tour covers some ground and is highlighted by an entertaining recount of Boston’s history.

Red Sox Game at Fenway Park

This wouldn’t be the Best Boston Itinerary if we didn’t include watching the Red Sox! End the first day of your Weekend in Boston Itinerary watching a baseball game at legendary Fenway Park. Built in 1912, Fenway reigns as the oldest MLB ballpark. It’s also one of the smallest so be sure to buy tickets in advance!

If the Red Sox are away or you are visiting Boston outside of the baseball season, you can take a Fenway Park Tour of the stadium instead. The engaging tour is a must for baseball fans. Get the details!

Pro Tip : You can catch a glimpse of the ballpark from the iconic Bleacher Bar. Occupying the former visiting team batting cages, The Bleacher Bar is situated beneath the Fenway bleachers with a window that provides a view of the outfield.

More Evening Boston Entertainment

Baseball isn’t the only sport in the city! The Boston Celtics (basketball) and Boston Bruins (ice hockey) teams play in the city center TD Garden Arena. The New England Patriots (NFL) play in nearby Foxborough at Gillette Stadium. 

Not a sports fan? No problem! Instead of including a sporting event in your Boston Weekend Itinerary, spend an evening in the bustling Boston Theater District watching a theatrical performance or comedy show. 

Day 2: Harvard, Cool Districts and Boston Beer

Today you’ll visit one of the most prestigious University campuses in the world, explore iconic neighborhoods and end the day on an brewery tour.

Impressive and classic, the Ivy League Harvard campus is just a short jaunt from Boston. Simple to reach using public transport, it’s a must to include in your 3 Day Boston Itinerary. Visitors can wander the campus to top sights, like Harvard Yard, then head to the Mr. Bartley’s Burgers, an institution since 1960 that serves up wicked good burgers.

Pro Tip : If you’d prefer not to discover Harvard sights on your own – join an informative student-guided tour to all the important spots!

Beacon Hill

When deciding what to do in Boston for a weekend, we highly recommend adding Beacon Hill to your list! Perhaps the most picturesque neighborhood in Boston, Beacon Hill (located on the north side of Boston Common) is home to landmark sights and quaint lanes.

Visit the golden domed Massachusetts State House, picture-perfect Acorn Street and the well-to-do Louisburg Square. The original Cheers bar, which provided inspiration for the 1980s sitcom of the same name, is located in Beacon Hill and is a great spot for lunch and a beverage.

Pro Tip : Visitors to the Beacon Hill neighborhood can also embark on the 1.5-mile Black Heritage Trail. The 10-sight route features houses and buildings that celebrate the history of the Black community and explains events that took place during the American Civil War. Follow the signs or get more information (and an audio tour) on the National Park Service website . 

South Boston

Next up on your Boston visit is the once rough and tumble neighborhood of Southie. Made famous in movies like Good Will Hunting and The Departed, the area has seen a flurry of gentrification in recent years. Southie has transformed from a gritty district into another one of Boston’s hip places to live, eat and play.

Now re-branded as SoBo – it still has a few old school haunts, but it is quickly becoming known for its upscale bars and gourmet eateries. Some of the places to visit in Southie include Dorchester Heights and the Monument, Joe Moakley Park and Medal of Honor Park. The Harborwalk, a 40-mile coastline path, connects Southie east to Pleasure Bay and Castle Island and south to the UMass Boston campus.

Pro Tip: Summertime visitors might consider heading to one of the South Boston beaches. Carson Beach and Pleasure Beach are our two top picks for sunbathing – but any stretch of the shoreline is fun to explore!

Boston Brewery Tour

Boston has a long and interesting history with beer. So naturally, when you plan a trip to Boston, hoisting a few pints should be on your list! 

The classic taverns and historic brewpubs – some of which date to the city’s founding in the mid-1600s – are excellent places to socialize. There are also a hefty number of Boston craft breweries where you can take a tour and get a taste as well. You can create a DIY brewery tour for your Weekend in Boston Itinerary with this list of breweries .

However, joining an organized Boston brewery tour is likely a lot more fun! Evening beer tours – like one of these – include samples, transportation and dinner.

Day 3: Boston on the Water

On the final day of your Boston trip itinerary, start off exploring the New England Aquarium. Next, get a taste of clam chowder, head out on the water and then eat a divine seafood meal on Boston Harbor. 

New England Aquarium

A must-see in Boston for 3 days, the New England Aquarium is a top attraction. The site should definitely be on a Boston family vacation itinerary.

Located on Central Wharf, the aquarium is a 4-level facility that features a massive fish tank and a variety of sea life. Top attractions are the penguins, seals and the you-can-touch tidepools. 

Pro Tip: Tickets can be purchased at the aquarium or visitors can use the Boston CityPass for entry. The card is also valid for harbor cruises, the Museum of Science and other Boston tourist attractions. 

Lunch of Clam Chowder at Boston Sail Loft

There are countless restaurants to get a good bowl of chowda in Boston, but far and away our favorite place is Boston Sail Loft. Perched over the water, the relaxing restaurant serves up a delectable and creamy clam chowder to a mix of locals and tourist.

Other dishes that we love at Sail Loft are the lobster roll – which is piled high with huge pieces of tasty lobster – and the absolutely decadent potato skins.

Pro Tip: If the weather is nice, try to get a seat outside on the small deck! 

Duck Boat Tour Boston

After spending the better part of three days in Boston on your feet, it’s time to sit back, relax and enjoy a ride. Wrap up your fun weekend in Boston on a Duck Boat Tour !

The famed Boston Duck Boat Tours use replica World War II amphibious road-and-waterway DUKW vehicles. They are able to take tourists for a spin around the streets and then a cruise on the river. The narrated tours offer a unique vantage point to some of Boston’s top landmarks while perched above the streets and on the Charles River. It’s the perfect final activity for your Boston Itinerary!

Pro Tip: If the Duck Boat just isn’t your style, instead consider taking one of the fun Boston Harbor cruises. Options include the historic Boston Harbor Cruise ( get the details) or the ever-popular Whale Watching Tour ( reserve your seat ).

Seaport District Restaurants

Seaport – or the South Boston Waterfront – is another recently revitalized area. Appealing to tech and innovation companies, the hip harbor front is a mixed-use Live, Work, Play district.

Seaport also features more than 80 places to eat, making it one of the top dining destinations in Boston. Home to numerous Boston seafood restaurants, we recommend eating at one of the city’s highly rated spots, like The Barking Crab or Legal Harborside.

Going out in Boston Seaport isn’t only about eating! For after-dinner drinks, head up to the swanky Lookout Rooftop and Bar or grab a swing at The Lawn on D. For something a little more down to earth, check out Harpoon Brewery.

More Things To Do in Boston, Massachusetts

We’ve highlighted the best activities in our Boston Weekend Itinerary, but fellow travelers may want to include these alternate attractions on their visit. 

Boston Museums

Learn about the city’s history or appreciate fine art at the best museums in Boston! You can easily add one of these fascinating museums to your 3 Days in Boston Itinerary by swapping out some neighborhood exploration or the Duck Boat Tour. 

Boston Tea Party Ships and Museum

Follow the story of the Boston Tea Party, which was a pivotal event in America’s history, through engaging exhibits, historic artifacts and interactive displays. Buy tickets!

Museum of Fine Arts Boston

The Boston Museum of Fine Arts – or MFA – features more than 450,000 works of art and entertains more than 1 million visitors each year. The space ranks as one of the largest art museums in the world with collections that span centuries.

Isabella Stewart Gardner Museum

From the late 1800s through the early 1900s, Isabelle Stewart Gardner amassed an impressive collection of art works. These include masterpiece paintings, tapestries and rare books. The world-class art exhibits are displayed in her beautifully designed, Venetian-inspired mansion. 

Mapparium Museum Boston

A gigantic stained-glass globe, the Mapparium Museum inside the Mary Baker Eddy Library introduces visitors to an intriguing look at the world circa 1935. Renovated for modern times, the 3-story museum now features a light and sound show.

Day Trips From Boston

We have packed our Boston 3-Days Itinerary to the brim, but there is more to see in New England! Travelers interested in regional exploration – rather than neighborhood discovery – might want to add a highly-rated tour into their Boston Itinerary. While there are numerous short trips from Boston, we are highlighting a few of the most popular.

Boston Tours to Martha’s Vineyard

A summer colony for celebrities and the wealthy, Martha’s Vineyard is a beautiful place to see. On a full-day tour from Boston, visitors travel by mini-coach along the coast to Cape Cod, then board a ferry to the island. Once on Martha’s Vineyard, participants can choose to explore on their own or upgrade their experience to a guided tour. Find out more!

Plymouth Colony Trip from Boston

Take a day trip from Boston back in time! Visit the Plimoth Plantation – a recreation of the 17th century Plymouth Colony established by Pilgrims. Then see Plymouth Rock – where the English colonists landed, and other historical sites on an all-day tour. Get the details!

Salem, Massachusetts

Well-known for the infamous Salem Witch Trials of 1692, Salem is a historic coastal town that is not far from Boston. Visitors can make the trip from Boston to Salem on their own using the convenient ferry and then join a walking tour once in Salem.

How Many Days Do You Need to Visit Boston?

Boston is diverse, historic and modern. Shabby and chic. Lively and relaxing. Therefore, determining how many days to spend in Boston can be tricky.

We love the city – and could easily spend weeks there. That said, to really get a good feel for it, we believe 3 days in Boston is ideal. That’s not to say if you are limited to a Boston One Day Itinerary you should skip it. Even with limited time, our sample itineraries will show you how to visit Boston!

Boston in 1 Day Itinerary

For a One Day Boston Itinerary, we recommend following Day 1 from above. If there is no sporting or cultural event during your visit, instead take the Brewery Tour or a Boston Food Tour .

Pro Tip : Visitors pressed for time can streamline their One Day in Boston Itinerary with a convenient self-guided tour on the extremely popular Boston Trolley ! 

2 Days in Boston Itinerary

To create the ultimate Boston in 2 Days Itinerary, we recommend simply following Days 1 and 2 of our above outlined itinerary. With this trip plan, you can get a really good feel for the city. If time allows, squeeze in the duck boat tour after exploring Southie for a fun way to finish off the trip!

However, if you are planning what to do in Boston for 2 days for a family trip, then we recommend using Days 1 and 3 from above. The aquarium and boat trip will likely be more interesting to kids than neighborhood discovery. 

Boston 4-Day Itinerary

To plan a Boston Itinerary for 4 Days, we recommend using our detailed outline for 3 days, then add one of the top Boston day trips. Alternatively, if you want to stay in the city and on foot, we recommend delving into a neighborhood that you skipped – or taking a longer stroll on the Harborwalk.

Boston Itinerary 5 Days

To create a 5 days in Boston Itinerary, we recommend using our above suggestions for 4 days then visit some of the city’s famous museums. You could also attend another event or take an additional day trip!

New York – Boston Itinerary

Since New York City and Boston are in close proximity, they make perfect destinations to combine on an US East Coast Trip. 

If you are planning an itinerary that includes both Boston and New York, start big with our 1-Week New York Itinerary – then get all our advice on how to experience NYC on a Budget . Furthermore, you can add other East Coast cities to your trip – like Philadelphia and Washington DC .

Top Travel Tips For Trips in Boston

Now that you know how to visit Boston in 3 days, we have a few final travel tips and packing hacks for your trip!

When To Visit Boston

One thing to consider when planning a Boston trip is when to go. Personally, we believe autumn is the best time to visit Boston. However, there are reasons for visiting Boston in every season! 

Summer is a fantastic time for a Boston visit. The weather is usually sunny and dry and the days are long – which is ideal for sightseeing. Plus, the Red Sox are playing! However, Boston summers can get hot and humid. Additionally, prices for hotels and flights tend to peak during the summer months. 

The fall is an ideal time for exploring Boston. With slightly cooler weather and fewer fellow tourists, it is delightful to explore Boston on foot during the autumn months. The fall is also a fantastic time to delve into the spooky side of Boston on the Nighttime Ghost Trolley Tour !

Many travelers dismiss the idea of visiting Boston in winter – but it can be very romantic. Although the weather will be brisk, it is perfect for cozying up in a classic tavern, ice skating at Boston Common and visiting the excellent museums.

Springtime in Boston can be hit or miss. Travelers who go to Boston in the spring will beat the crowds (and likely find better prices, too). If the weather cooperates, it is a great time to see Boston and enjoy the spring blossoms!

How To Get to Boston

Boston can be reached by car, bus, boat, train or plane. On our Boston weekend trips, we have always flown into Boston Logan International Airport. Read our hacks for the best airfares , then start your search for flights to BOS on SkyScanner !

Boston Airport to Downtown Boston

To get from the Boston Logan Airport into the city, visitors can use public transportation, Uber/Lyft, private transport or  shared transport .

To get from Logan Airport to Boston via public transportation, it’s best to take the free Silver Line SL1 Bus into Downtown Boston. The last stop is South Station, which has Boston subway and other bus connections. 

Where To Stay in Boston for a Weekend Trip

We believe the best place to stay in Boston is downtown. A central location will put you within steps to our outlined activities of what to do in Boston in 3 days. 

There is a wide range of Boston accommodations – from luxury properties to Airbnb apartments to budget hotels.

Boston Airbnb

Generally, we prefer staying in Airbnb apartments. We have found that we can usually get more space (including a kitchen to make breakfasts) for less money than hotels. 

That said, on a short Boston weekend trip, it might not be the best option. Airbnb fees can add up quickly and it can be time-consuming coordinating check-in and check-out with your host. 

Weekend Itinerary Boston Hotels

Staying in a hotel is ideal on a weekend trip to Boston. While they do tend to be pricey, weekend Boston visitors can sometimes score a deal on downtown hotels that typically cater to business travelers. 

Top choices for the best location include Club Quarters (an affordable option in the heart of town) and Omni Parker House Hotel (a luxury stay that is close to everything). The citizenM is a hip and modern hotel in the nearby West End and can be a fun place to stay for Boston weekends!

What To Pack For Your Trip to Boston

Packing can be a chore! Be sure to read our Ultimate Packing List , but we have a few specific packing tips for your trip to Boston as well. Grab your FREE Packing Checklist and let’s get started!

Boston Weather Apparel

The weather in Boston is unpredictable. Summers are typically hot and humid and winters can be cold and wet – and spring and autumn can be anything in between!

For your trip to Boston for the weekend, be sure to pack clothing that can be layered. Regardless of the season, bring a travel umbrella or packable raincoat . 

Durable Walking Shoes 

In our 3-Day Boston Itinerary, we cover some ground! Be sure to pack comfortable travel shoes for your trip. Flat, rubber-soled shoes – like these Columbia shoes for women or Merrell trail shoes for men – are what we wear while walking Boston city streets.

Travel Camera for the Best Photos of Boston

As one of the most historic cities in America, Boston is gorgeous. If you are anything like us, you will be snapping a ton of pictures during your weekend getaway to Boston.

Rather than messing with your phone, we recommend upgrading to an actual camera . We use a Canon Rebel with a 18-135mm lens that takes great pictures…and it is easy to use! Best of all, it comes with a complete kit, which is a perfect budget option for beginner photographers !

Weekend Trip Boston Day Bag

Whether you travel with a backpack or a suitcase , you will definitely want a great day pack for your Boston trip. We like to carry these small backpacks for all our adventures. They are perfect for securing our phones, keys, camera and all of our everyday travel items .

Start planning your trip to Boston, USA ! Search for the lowest airfares , the best accommodations and fun things to do …then start packing !   Want more travel advice? Head over to our Travel Planning Page for tips on traveling – and for country-specific information, take a look at our Travel Guides Page !

More USA Destinations: East to West

There is no shortage of places to visit in the United States! Get inspired for your next trip with our list of the Best USA Destinations for Weekend Trips and check out our Top Underrated US Spots !

Are you venturing out West in the US? Be sure to read our detailed guides to Oregon , California  and Montana. How about a Weekend in San Diego ,  San Francisco , or the Mile High City of Denver ? We also have great tips for visiting Seattle , Portland, OR or Vancouver WA or an adventure in Malibu , Phoenix or Flagstaff AZ !

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3 Days in Boston: The Perfect Weekend Itinerary

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Known as the “Cradle of Modern America,” Boston is one of the most historic cities in the United States. Everywhere you look in Boston, you’ll stumble across a place of historical significance, from the “Tea Party” at the Boston Harbor to the Old North Church, where the two lanterns once alerted that the British soldiers were coming up the Charles River. 

Today, Boston is not only a hub for history but also beautiful art and architecture, one-of-a-kind shopping, and delicious dining. Boston is also known to be a college town, with over 100 schools in the area. 

And those colleges affect when the best time to go to Boston is. Unlike many other travel destinations in the United States, Boston is often at its quietest in the summer, when most of the college students have returned home at the end of their semester. So, if you’re looking for a more peaceful visit, you may want to go in the summer! 

That said, there’s no bad time to visit Boston, as long as you’re willing to brave the cold. In the winter, Boston temperatures can hover around freezing, so be sure to bundle up. But if you’re ready to travel in the winter, you’ll discover beautiful holiday displays, ice-skating on the iconic Frog Pond, and the wonderful Beacon Hill Holiday Stroll, where you’ll do some holiday shopping with a hot cocoa in hand. 

Spring, when the weather warms up a bit, brings about two of the busiest times to visit Boston: the Boston Marathon weekend and St. Patrick’s Day. The Boston Marathon, held on the third Monday of April, known as Patriot’s Day, is a Boston tradition dating back to 1897. It’s the world’s oldest marathon and brings in over 20,000 runners from around the world each year.

Boston has a strong Irish heritage, which is why it’s often considered one of the best places to be for St. Patrick’s Day. From the annual parade to the traditional Dropkick Murphys concert, people come from all over to celebrate the holiday here.

Planning a long weekend trip in Boston? With so much to do and see in this historic city, it’s tough to know where to start. That’s why we’ve put together a 3-day Boston itinerary to help you see all that you can of Boston. Follow these recommendations, from where to eat to what to do, and you’re bound to have an amazing time exploring Beantown!

If you’re still deciding where to stay then make sure to check out our article on the  best boutique hotels in Boston !

Disclaimer: This post may contain affiliate links. If you make a purchase or booking through one of our links we may earn a small commission (don’t worry, it’s at no extra cost to you).

How to Spend a Weekend in Boston, Massachusetts

Getting around boston.

If you’re flying into Boston, you’ll most likely land at Boston Logan International Airport. To get into the city, you have many different options. You could always simply hop aboard the T, Boston’s mass transit system that connects the city and surrounding communities. Both the Blue Line and the Silver Line have ways to get you from the airport into the city.

You could also take the Logan Express, which will get you between the airport and Boston’s Back Bay. For a more scenic form of transportation, you could also take a water taxi from the Logan Airport to several areas around Boston, like the North End.

Not only is it unnecessary to rent a car to get around Boston, but it’s also not recommended. Boston is a very old city, and the streets are rather narrow and often difficult to navigate if you’re new to the area. Some areas of Boston don’t allow cars at all, meaning that you’ll have to park rather far away to get to those locations. 

The city is very walkable, with many attractions within a small area. If you rent a car, you may find yourself simply leaving it parked all day. Though, you’ll have trouble finding parking in the first place. Boston’s public transportation system will get you around the city just fine. Get yourself a Charlie Card on your first day in town, and use it throughout your trip to hop abroad the T. 

Boston Weekend Itinerary – Day 1

Compared to many of the United States’ major cities, Boston is fairly small, but there’s so much packed into it. So, it’s hard to decide just where to start. But for the first day of your 3-day Boston vacation, you should start over in the Beacon Hill area. 

Beacon Hill’s Acorn Street

Beacon Hill is a historic neighborhood in Boston that’s as pretty as a picture. In fact, Beacon Hill’s Acorn Street is purportedly the most photographed street in the country. With its cobblestone roads lined with antique lanterns and rows of brick houses, it’s one of the most beautiful areas in the city!

Beacon Hill’s Charles Street

Over on Beacon Hill’s Charles Street, you’ll find a breakfast place that should kick off your 3 days in Boston. The Paramount is breakfast at its best, and it’s been serving up its comforting treats since 1937. You can’t go wrong with its buttermilk pancakes, but for an even more decadent meal, grab the Nutella waffle.

Once you’re done eating, you’ll want to spend some time exploring Charles Street and walking the famous hills of Beacon Hill. Charles Street is filled with boutique stores, chocolate and other sweet shops, and places to sip everything from fine wines to fresh juices. 

Get Your Hop-On, Hop-Off Trolley Ticket

Take a short scenic walk from Beacon Hill to the lovely and vibrant Chinatown, where you’ll find a one-of-a-kind spot for lunch. Empire Garden serves dim sum daily, but while the food and cocktails are delicious, you’re really going here for the ambiance. 

This restaurant is built inside an abandoned theater. In the enormous dining room, you’ll find intricate murals on the walls, chandeliers hanging from the high ceilings, and gold trimming everywhere you look. It’s a picture of grandeur! 

Boston Common and Boston Public Garden

After you’re done dining, head over to the nearby Boston Common and Boston Public Garden. Despite being directly next to each other, these public areas have their own unique personality and features. They’re also best to visit at different times of the year.

The best time of year to visit the Boston Public Garden is during the spring and summer, when you can spend the day strolling around the flowers or taking a tour of the lake on the famous Swan Boats . But the best time to visit the Boston Common is late in the year when the Frog Pond becomes an ice-skating rink and the park is illuminated with hundreds of twinkling lights. But no matter when you visit, be sure to take a ride on the Boston Common’s carousel and say hello to the “Make Way for Ducklings” bronze statues in the Boston Public Garden.

Omni Parker House (and The Last Hurrah)

When you’re ready for dinner, venture over to the Omni Parker House , a historic hotel that also happens to be the home of the Boston Cream Pie. While the main restaurant, Parker’s Restaurant, is only open for breakfast and lunch, you can grab dinner and a drink at the hotel’s whiskey bar, The Last Hurrah . 

And don’t worry – you can get a Boston Cream Pie for dessert at the bar. You can also get a Boston Cream Pie in cocktail form if you just can’t get enough of Boston’s famous treat! 

Book a Room at the Omni Parker House

Boston’s Theater District

End your night by taking in a show in Boston’s Theater District. You have plenty of options for seeing a live production in this area of Boston, but keep in mind that you may need to buy tickets in advance, depending on what you’d like to see. 

The Boston Opera House is a beautifully ornate theater where you can see spectacular productions of touring Broadway shows. Although you should most likely get tickets ahead of time to see one of these shows, some performances also have lotteries. If your name gets picked for a lottery, you’ll get discounted tickets for the show that day.

At the Colonial Theatre , owned by Emerson College, you can often see shows before they premiere on Broadway at much less expensive rates. The Wang Theatre was designed to look like the Paris Opera House, so it’s the picture of opulence. Here you’ll find touring comedians, singers, and much more. No matter which theater you head to, you are in for a night filled with world-class entertainment. 

Boston Weekend Itinerary – Day 2

For the second day of your 3-day trip to Boston, you’ll start at the Boston Public Market . This year-round indoor market offers artisanal treats from local New England vendors. Here you’ll find 30 artists, bakers, butchers, and so much more selling seasonal, locally-sourced items. 

For your breakfast on the second day of your 3 days in Boston, take a walk around the market and pick out your favorites. Grab a bagel from the Bagel Guild, make a crepe at the Bon Appetit Creperie, or treat yourself to a Boston Cream Donut at Union Square Donuts. 

Boston Cream Donut

For a drink, order a latte at George Howell Coffee or grab some green juice at Mother Juice. When you’re done eating, take a walk around the market and see what else you may want to pick up. There’s plenty to explore here, from stonework to allergen-friendly truffles.

Experience a Boston Underground Donut Tour

Faneuil Hall Marketplace

Next up, you’ll head to nearby Faneuil Hall, a historic area that has served as a meeting hall and marketplace for more than 270 years. Walk the cobblestone street and take in the history of this cultural hub. Take a stroll through the Faneuil Hall Marketplace , also known as Quincy Market, to discover tons of shops, restaurants, and stalls. 

From shops with handmade Christmas ornaments to comic book stores, there’s something for everyone at this fun location. When you’re ready for lunch, you have many options here, but if you want an iconic Boston treat, get a bread bowl of clam chowder from the Boston Chowda Co. 

Boston Chowda Co

From Faneuil Hall, take a walk over to the Boston Harbor, where you’ll find the next item on your Boston itinerary. What you do next will depend on the seasons. If you’re visiting in spring, summer, or early fall, hop aboard one of Boston’s famous Duck Tours . 

These tours launch from three locations, one of which is near the New England Aquarium. A colorful cast of characters called the ConDUCKtors will take you aboard a DUCK, an authentic World War II amphibious vehicle. 

On your tour, you’ll see landmarks of all kinds, from the Old State House to the iconic “Cheers” pub, while the ConDUCKtors tell you little-known facts about these locations. But since you’re in an amphibious vehicle, the big treat of this tour is that you’ll splash down in the Charles River, where you’ll get an incredible view of the Boston skyline. 

Book a Boston Duck Tour

New England Aquarium

However, due to Boston’s climate, the Duck Tours don’t run from late November to early spring. If that’s when you’re visiting for your long weekend in Boston, you should instead explore the Boston Harbor and head to the New England Aquarium . 

This aquarium, which is dedicated to conservation and using innovative solutions to solve threats to ocean life, is the perfect spot for an afternoon of fun and education. From the busy and vibrant Indo-Pacific Coral Reef exhibit to the many penguins of the Penguin Colony exhibit, it’s easy to spend a whole day watching these majestic creatures.

Union Oyster House

When you’re done with your tour or your day at the aquarium, it’s time to head to dinner. And there’s perhaps no more iconic dinner spot than the Union Oyster House . This seafood restaurant is not only Boston’s oldest restaurant, but it’s one of the oldest restaurants in the United States!

Dating back to 1826, this National Historic Landmark has maintained its original style after all these years. Dining at this little piece of history is always a delight. Because this landmark is so famous, it’s often busy on weekends, so be sure to reserve a table in advance.

Dessert at the Union Oyster House may be delicious, but we recommend going on a little walk to the North End to take part in the “Great Cannoli Debate.” Some say the best cannoli can be found at Mike’s Pastry . Others say it’s at Modern Pastry . As for us, we like Bova’s Bakery . So sample your way around the North End and pick which cannoli you think ranks the best.

Boston Weekend Itinerary – Day 3

Newbury street.

For the last day of your 3 days in Boston, you’re going to want to start over on Newbury Street for one of our favorite Boston brunch spots, Trident Booksellers & Cafe . If you’re a book lover, you’ll fall in love with this place, which serves up breakfast favorites inside an indie bookstore.

Put your name down for a table and then wander your way around the shop, searching for your next great read. Then, when the table’s ready, order off their massive menu, filled with seasonal treats. Although you can’t go wrong with anything on the menu, we love the Lemon Ricotta Stuffed French Toast, made with thickly sliced challah bread.

Then, head out onto Newbury Street for some shopping. Newbury Street is famous for its restaurants, boutiques, and one-of-a-kind stores. For magical trinkets and a little bit of pixie dust, visit the famous Fairy Shop. 

And for handmade chocolates like you’ve never seen before (including in the adorable shape of penguins), stop by L.A. Burdick Handmade Chocolates . If you’re an art lover, you’ll also find plenty of art galleries dotting this street.

Trinity Church and Old South Church

From Newbury Street, take a walk over to Copley Square, a famous public square in the Back Bay neighborhood. Take in the art and architecture of this historical area. Here you’ll find the stained glass-filled Trinity Church, the enchanting green-domed Old South Church, and the massive Boston Public Library . Take some time exploring these landmarks, as the interiors are just as incredible as the facades.

Boston Public Library

For lunch, visit nearby Saltie Girl , which serves up one of the best versions of a New England classic: the lobster roll. This Boston favorite is often busy, especially on weekends, so you may want to make a reservation for lunch. If you’re traveling with seafood lovers, be sure to order a Seafood Tower, which is filled with plenty of sustainably-caught seafood options.

From there, it’s time to hop aboard the T and head to Fenway Park . No matter what time of year you visit for your long weekend in Boston, you should spend some time over in the Fenway area. If you’re a baseball fan, definitely look for tickets for a game at this historic location. Fenway is unlike any other baseball field. There’s history in every seat! 

Fenway Park

One thing to note, however, is that you may want to skip visiting Copley Square if you’re going to a game. The T is often crowded on game days, and it may take longer to get to Fenway than you’d expect. So, it’s worth heading over to Fenway a little early. If you arrive long before the game starts, don’t fret. You can always spend some time walking the Jersey Street pedestrian mall, formerly known as Yawkey Way.

If your 3-day trip to Boston isn’t during baseball season, you should still pay Fenway a visit. You can take a tour of the park, or you can check out what events are happening in the stadium. The park does a concert series every summer, so you may just see your favorite performer at this iconic field. 

Finish off the night and your long weekend in Boston with dinner and drinks at the Bleacher Bar . This unique bar is actually beneath Fenway Park’s bleachers and offers you a view of centerfield. Even if there’s no game happening, you’ll love taking in the sights of Fenway from this famous bar. Grab yourself a drink and a Bleacher Burger, and enjoy dining at this historic park!

Take a Fenway Park Walking Tour

More Places to Eat & Drink in Boston

Try an award-winning doughnut at Blackbird Doughnuts : This Boston staple started in the South End, but you’ll now find them at their flagship location, as well as in three other Boston locations: Fenway, Beacon Hill, and the Financial District. For a truly unique doughnut, try the Everything Bagel, a brioche doughnut with cream cheese filling topped with everything bagel spice.

Venture over to Cambridge for the famous Mr. Bartley’s Burger Cottage , a Harvard Square institution since 1960: Known for its massive burgers and legendary frappes, this place is comfort food to the max. We love The Yoda, a burger topped with pesto mac and cheese.

Grab a slice at Regina Pizzeria : This North End staple has been serving up some of the best pizza in Boston since 1926. This pizzeria boasts a massive menu, but we think the traditional Cheese Pizza is still the way to go.

What to do if you have more than 3 days in Boston

Meet your favorite authors at the Boston Book Festival : Happening every October in Copley Square, the Boston Book Festival invites the best authors around to partake in a weekend filled with literary events. Past speakers include Lemony Snicket, Rick Riordan, and Margaret Atwood. These conversations and events happen throughout Copley Square, so you’ll get to be inside beautiful locations like the Trinity Church while you listen to your favorite writers talk about their craft.

Take a Freedom Trail tour :

The Freedom Trail is not to be missed if you’re a history lover. This walking tour takes you to 16 historical locations that were important to the Revolutionary War, like the Paul Revere House and the Old South Meeting House. While you could walk this trail by yourself, you also have several options for guided tours, complete with a tour guide dressed in period garb.

Explore around Boston Freedom Trail

Board the trolley for the Ghosts & Gravestones Tour : For a different side of Boston’s history, this nighttime tour will show you the haunted parts of this historic city. On this Trolley of Terror, you’ll be led through tales of the not-so-happy haunts of the Omni Parker House, the biggest grave-robbing scandal ever to hit New England, and much more.

Venture to Boston’s Haunted Burial Grounds

See a show at the Brattle Theatre : If you’re a movie lover, you should head to this historic Cambridge movie house, known for its stunning architecture and special event screenings. There’s something new playing on the one screen here each night, from new award winners to classic favorites, so be sure to check the website to see what’s being shown.

Stroll through the Isabella Stewart Gardner Museum :

This art museum is a Venetian palace surrounded by lush greenery, housing incredible American, Asian, and European art. It’s a remarkable place to spend an afternoon and one of the best museums to be found in Boston.

We hope you enjoy your weekend trip to Boston! Should we add something else to our 3-day Boston itinerary? Let us know in the comments.

Planning a trip to Massachusetts? Check out our favorite travel guides and resources!

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Jacqueline is a writer and editor pursuing the freelance life to explore the world. Born and raised in New Jersey, she spent her college years in Boston before settling down with her partner and puppy in Monterey, California. When she’s not writing, you can often find her planning her next trip. Road trips are her favorite, whether it’s driving across the country or simply exploring a new city in her own backyard. She loves uncovering the history of every new place she goes. Jacqueline has a restless passion for learning and makes it a goal to pick up a new skill every year. She’s picked up embroidery, crocheting, knitting, and cross-stitching, but she’s hoping to master more languages to help her in her travels. She’s also a published author, with short stories and poetry appearing in several anthologies.

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Weekend in Boston: The Perfect 3-Day Itinerary

Last Updated on March 6, 2024

Looking to spend a weekend in Boston? We have visited Boston a few times now, and have designed this 3-day Boston itinerary to help you make the most of your escape.

Aptly named the “Cradle of Modern America,” Boston is known as the nation’s pioneer, where the first subway system, first public school and first public park were created. For a city with so many impressive accolades to its name, Boston is welcoming and charming, and gives off a big town feel.

For that reason, it makes for an excellent weekend trip for good reason. Boston is a city where history and modernity perform a tango, and every cobblestone has a story to tell.  Its blend of historical charm with modernity, coupled with unpredictable weather, Boston warrants advanced preparation before hopping on a plane. Here is my detailed Boston itinerary for those who intend to spend a weekend in Boston. I promise it’ll make you want to come back for more!

Table of Contents

Visit Historic Freedom Trail

Check out instagram-worthy beacon hill, head to chinatown for lunch, visit boston common and boston public garden, join boston ghosts and gravestones trolley tour, visit the museum of fine arts (mfa), check out isabella stewart gardner museum, visit fenway park, visit faneuil hall, join duck tours, visit the new england aquarium, check out boston’s theater district, nantucket island, provincetown, how to get around boston, best time to visit boston, budget: hi boston, mid-range: copley house, luxury: ac hotel by marriott boston cleveland circle, enjoy your weekend in boston, 3 days in boston itinerary, boston itinerary day 1: learn boston’s history.

Begin your Boston weekend trip by strapping on your comfiest walking shoes and hitting the Freedom Trail . Embark on a 4km journey through downtown Boston that leads you through 16 distinct historical sites, several of which were pivotal in the American Revolution. Trace the path of the founding fathers as you stroll through the pages of American history along this trail.

Step into history at the iconic Boston Common , the oldest public park in the US. As you venture north from the park, a historical journey unfolds through the charming North End. Discover landmarks like the Massachusetts State House , the solemn King’s Chapel Burial Ground, the Old South Meeting House, and the Old State House, among others.

The Old State House stands witness to the Boston Massacre , an event that sparked the flames of the Revolutionary War. While most sites here are free to access, the Old State House requires an entrance fee. If you want to learn all about Boston’s history, I recommend booking a guided tour of the Freedom Trail .

Beacon Hill, a storied enclave in Boston, unfolds like a picturesque postcard. Renowned for its timeless charm, Acorn Street is one of the most photographed streets in the US . The cobblestone pathways adorned with vintage lanterns and brick residences make this neighborhood an aesthetic masterpiece.

Next up; head to Charles Street, the heartbeat of Beacon Hill, where boutique stores beckon, chocolate confections tempt, and sweet shops entice. While here, explore, and discover everything from fine wines to refreshing juices along this delightful avenue.

From Beacon Hill, take a short stroll to the enchanting and lively Chinatown. There is a chic eatery in Chinatown that will cater to all your gourmet needs. Empire Garden not only offers delectable dim sum every day, but it’s the ambiance that truly steals the show.

Found within the walls of a former theater, this restaurant is a spectacle in itself. It’s a visual feast, a true embodiment of grandeur that adds extra magic to your dining experience. If you are a foodie then you will love this place.

After that scrumptious meal, make your way to the nearby Boston Common and Boston Public Garden . Established in 1839, the Boston Public Garden was the first public botanical garden in the US. Unlike the neighboring Boston Common, the Boston Public Garden has a distinctly ornamental style.

Enclosed by an elegant Victorian cast-iron fence, the public garden showcases winding pathways adorned with statues, fountains, and a diverse array of trees and plants. There is also a six-acre pond offering visitors the delightful option to embark on swan boat rides.

Boston Common has been a pivotal player in shaping the history of conservation, landscape architecture, military and political affairs, and recreation within Massachusetts. Its historical significance for the city also reflects comparable models implemented by American conservationists across the nation.

As night falls, embark upon the spine-chilling journey aboard the “Trolley of the Doomed” and delve into the eerie side of Boston. Known as the best ghost tour in Boston , this tour is realistic and dramatic, and will definitely send a chill down your spin. Discover the supernatural antics unfolding at the Omni Parker House , unravel the mysterious tale of the Boston Strangler, and pay a visit to King’s Chapel cemetery, where the bones of the departed once served as a gruesome currency for Ephraim Littlefield.

Boston Itinerary Day 2: Explore Fenway Park

On day two of your weekend trip to Boston, get ready to explore some of the city’s finest museums and the iconic Fenway Park neighborhood. Kickstart your morning with a delightful breakfast at Cafe Bonjour , where their menu is a true culinary delight. Indulge in classics like hazelnut spread and strawberries or savor the sweet simplicity of banana fosters. The chic eatery also offers a Strawberry Patch featuring house-made rhubarb jam crowned with a luscious lemon custard sauce.

Boston is home to several museums making it incredibly hard to pick out a few. However, the Museum of Fine Arts is a must-visit gallery for your Boston itinerary. Housing more Monets than any museum outside Paris, an assembly of Japanese art, priceless treasures from Egypt, and an array of American art, this museum is a global artistic haven. With each step, transport yourself to different ages, as you engage with exhibits designed to inspire your artistic responsiveness.

In the heart of Boston, where art and audacity join hands in a dance of whimsy, lies the Isabella Stewart Gardner Museum . A visit to this cultural haven is like stepping into a time-traveling tea party hosted by a spirited art aficionado.

Isabella Stewart Gardner, the audacious soul behind this artistic haven, orchestrated the creation of her wide-ranging playground, and the result is nothing short of magical. Step into the enchanting courtyard, a lush oasis surrounded by balconies adorned with flowers and sculptures. It’s like stumbling upon a secret garden amid the bustling city.

Fenway Park ‘s legacy is intimately intertwined with the soul of Boston, and for city residents, this iconic ballpark is nothing short of sacred ground. Located in the Fenway neighborhood from which it takes its name, its verdant structure stands tall. The glow of night games illuminates the Boston skyline, visible from miles away.

A guided tour of Fenway Park is the best way to explore the entirety of the stadium while delving into the rich history of the Sox. This excursion offers unobstructed views of the ballpark, allowing you to see iconic features like the Green Monster, the press box, and even the rooftop vegetable garden.

Led by passionate Red Sox guides, this tour promises an insider’s perspective. If you visit Boston during baseball season, make sure to attend a game – it’s the best way to spend your Friday night in the city.

Boston Itinerary Day 3: Venture Further out

For the last day of your Boston itinerary, get an early start at the Boston Public Market . The year-round indoor marketplace showcases a delectable array of artisanal delights sourced from local New England vendors. Start your morning by picking out the city’s breakfast favorites. Choose a bagel from the Bagel Guild , a delicious crepe at the Bon Appetit Creperie , or indulge in a Boston cream donut at Union Square Donuts .

After breakfast, your next destination will be Faneuil Hall, a storied locale that has served as a meeting hall and marketplace for over 270 years. Wander along the charming cobblestone street, immersing yourself in the rich history of this cultural focal point. Explore the vibrant Faneuil Hall Marketplace (Quincy Market) lined with shops, restaurants, and stalls.

When it’s time for lunch, you’ll find numerous options in this area. However, for an authentic taste of Boston, order a bread bowl of clam chowder from the renowned Boston Chowda Co. – a truly iconic treat!

Guiding you on this adventure are ConDUCKtors, a lively bunch ready to welcome you aboard a World War II amphibious vehicle known as a DUCK. As you traverse the city, catching glimpses of landmarks like the Old State House, the ConDUCKtors regale you with intriguing tidbits about the sites.

The real highlight, however, is the amphibious nature of your vessel. Brace yourself for an exhilarating splashdown in the Charles River, treating you to an unparalleled view of the Boston skyline. Note: The Duck Tours remain closed from November to early spring.

Immerse yourself in a world of conservation and inventive solutions at this aquarium true to its mission of addressing challenges facing ocean life. Spend an enriching afternoon exploring the captivating Indo-Pacific Coral Reef exhibit, or watch the playful penguins at the Penguin Colony exhibit. The aquarium is a destination that combines entertainment and education, making it ideal for an afternoon of exploration.

End your weekend trip to Boston with a captivating performance in the Theater District. There are countless live productions here. However, we advise you to secure tickets in advance based on your preferences.

The Boston Opera House , an opulent venue, hosts dazzling live productions of touring Broadway shows. Alternatively, explore Emerson College’s Colonial Theatre, where you can often catch shows before they make their Broadway debut at more affordable rates.

The Wang Theatre , fashioned after the Paris Opera House, exudes opulence and hosts a diverse array of performances. Regardless of your choice, your night promises to be a world-class entertainment experience in the heart of Boston’s cultural scene.

Boston Travel Guide

Day trips from boston.

If you have a bit more time, we’ve concocted a whimsical guide to Boston day trips that will have you escaping the city limits faster than you can say “lobstah roll.”

Nantucket Island is famed for its pristine sandy beaches, picturesque gray-shingled cottages adorned with vibrant blooms, and an iconic lighthouse that stands as a beacon of coastal charm. To catch a ferry to Nantucket, you need to venture to Hyannis on Cape Cod. Once there, seize the freedom to tailor your day to your desires. Pedal through the island’s scenic paths on a rented bike, unwind on the sun-kissed beaches, indulge in delectable fresh seafood, or go on a scavenger hunt – the choice is yours.

Provincetown is the eclectic gem at the tip of Cape Cod where the lobster traps are as colorful as the characters you’ll meet. Forget what you know about quaint New England towns; Provincetown is a vibrant kaleidoscope of art, culture, and just the right amount of quirk.

To get there, take the Provincetown Fast Ferry departing from Long Wharf, just next to the New England Aquarium in the heart of Boston. In just 90 minutes, you’ll disembark at in Provincetown, ready to explore the vibrant charm of this coastal haven.

The opulent Newport from the Gilded Age still command admiration with their grandeur—after all, that was their primary purpose. If you find yourself with time for just one estate tour, make it The Breakers. Located close to the International Tennis Hall of Fame, the Audrain Auto Museum offers a dynamic exhibition of remarkable cars within a stunning Art Deco structure.

To reach Newport, take a commuter rail from South Station into North Kingstown (a journey of 1.5 to 2 hours) and then take a taxi or Uber to reach Newport. Keep in mind that the train schedule has limited daily trips, so planning ahead is essential.

For your weekend trip to Boston, we recommend packing comfortable and season-appropriate footwear because you’ll be doing lots of walking. Downtown Boston is compact, spanning about two square miles, making it an easily navigable area on foot. Despite subway stations in the city center being close to each other, walking makes more sense than waiting for one.

Should you decide to navigate the city using the subway system, aka the ‘T,’ consider a seven-day unlimited pass or a reloadable plastic CharlieCard . The seven-day pass makes sense for stays longer than a couple of days, covering rides on the Charlestown ferry. If you prefer a pay-as-you-go approach, the CharlieCard offers a 50-cent discount on regular subway fares ($2.25 instead of $2.75).

Unless you opt to stay outside the city center, a car is not essential for your weekend in Boston. Most hotels in Boston tack on a daily parking fee of over $40, and securing street parking frequently demands a neighborhood permit which is designated for residents only.

While summer is the peak tourist season in Boston, fall emerges as a strong contender for the best time to explore the bustling city . By September, the weather takes a turn towards drier and more pleasant conditions, with October showcasing a vibrant display of foliage. Spring is a great alternative despite bringing a bit of uncertainty in terms of weather, but the blooming blossoms add a captivating touch.

Where to Stay in Boston

Boston’s hotels and Airbnb rentals often spring surprises on its visitors, with third-floor walk-ups, steep staircases, creaky floors, or more snug quarters than they might expect. If you’re seeking modern comforts, please verify whether a location offers elevator service, air conditioning, and other amenities, as these conveniences aren’t guaranteed.

Scoring super cheap accommodation in Boston can be quite the challenge, so look no further than HI Boston in Downtown. Priced at a wallet-friendly $40 per night, this hostel is a top-notch choice. Boasting a communal kitchen, common area, and meeting rooms, HI Boston goes the extra mile for budget-conscious travelers. Book your stay here.

Nestled in the pulsating core of Back Bay, Copley House features apartment-style rooms and suites set within the timeless charm of traditional brick-row houses. Copley presents diverse apartments catering to every kind of traveler. Plus, you will find so many shops and restaurants along the trendy Newbury and Boylston Streets. Book here.

Nestled just 3 miles away from Fenway Park, the AC Hotel offers comfortable lodgings with a fitness center, private parking, a shared lounge, and a bar. Priced at $261 for a weekend night, this hotel easily connects to the entire city through the MBTA Green Line. Book here.

Feel free to print out this Boston itinerary and bring it with you on your weekend getaway! I have packed this itinerary with all the best things you can do in Boston in 3 days, so get ready to have a blast.

Be sure to leave a comment below if you have any questions. Read more of my US articles to get idea for your next weekend trip:

• Weekend in New York
• Weekend in Seattle
• Weekend in Los Angeles
• Weekend in San Francisco
• Weekend in Miami
• California Road Trip Itinerary
• Arizona Road Trip Itinerary
• Florida Road Trip Itinerary
• Best National Parks in USA

Disclaimer: This post contains affiliate links to companies I use and trust. I get a small commission when you click on my links, at NO EXTRA COST TO YOU.

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Nellie Huang

Nellie Huang is the founder of WildJunket. Originally from Singapore, Nellie has traveled to over 150 countries across 7 continents. As an accomplished travel writer, she has written for BBC Travel, CNN and Rough Guides . She is also the author of five travel books, including the latest Lonely Planet's Mexico guidebook. Read more about her here and follow her on Facebook and Instagram .

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This Boston itinerary is a traveler’s dream! The curated selection of activities ensures a memorable experience. I’m excited to follow your recommendations and explore the charm of Boston. Your blog provides a fantastic guide for anyone planning a weekend escape. Thanks for the inspiration!

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One Weekend in Boston, MA: A 3-Day Boston Itinerary

Boston, MA is a city known for its deep historical roots, gorgeous architecture, and countless activities to enjoy. There’s truly something for everyone which makes Boston the perfect destination for a weekend trip. Read on for recommendations on how to make the most out of a 3-day trip to Boston! 

This site contains affiliate links to products. I may receive a commission for purchases made through these links at no extra cost to you.  There are  only products included that I truly love. I APPRECIATE your support!

Table of Contents

How do I get to Boston?

One of the most convenient ways to get to Boston is through Boston Logan International Airport. Driving to the city is also a popular option, as Boston is located only a few hours outside of New York City, Philadelphia, and other major cities on the East Coast.

The Massachusetts Bay Transportation Authority offers several options for public transportation in the Boston area. Buses, commuter rails, and the subway are all common ways to navigate the city, and certain areas are very walkable. A rental car is not necessary to enjoy Boston, as there are also plentiful rideshare services available.  

Tip!! Use the Discover Cars Search Engin e to find the best deal on cars for your weekend in Boston.

What is the best time to visit Boston?

Summer and fall are the best seasons to visit Boston for pleasant weather and to enjoy seasonal outdoor activities. While summer is one of Boston’s most popular seasons, it is worth a visit if you’d like to attend some baseball games or outdoor concerts. Fall, meanwhile, will bring cooler temperatures that make exploring the city on foot very enjoyable. Fall is also a great time to visit if you are a fan of fall foliage. 

Where should I stay in Boston?

Boston is home to a number of distinct areas and neighborhoods, but two great options to consider are downtown and Back Bay . If you want to be in the heart of the action and have the ability to walk among restaurants, shops, and activities, downtown is the place to be.

Staying downtown will put you near some of Boston’s most popular attractions, and you’ll be in the perfect place to explore the city’s nightlife. The Bostonian Boston is an upscale hotel with a reasonable price tag in the heart of downtown, while CitizenM Boston North Station Hotel is a little more pricey with sleek, luxurious rooms.

For fans of architecture and history, Back Bay is another great option as well. Back Bay is located along Newbury Street, one of Boston’s best areas for shopping and dining. Back Bay is full of historical buildings and homes and is considered a very upscale neighborhood within Boston. Hilton Boston Back Bay offers a standard hotel experience while The Charlesmark Boutique Hotel is perfect for those seeking a more unique stay.   

Sample 3-Day Boston Weekend Itinerary

Day 1 in boston.

Start your morning right with a cup of coffee from the iconic Polcari’s Coffee . Polcari’s has been in operation for almost 100 years, making it a true Boston institution. The shop serves up classic drinks and Italian delicacies, and is one of the city’s most well-known and loved coffee shops.

Take your coffee to-go and enjoy a stroll along the Freedom Trail , a 2.5-mile-long path through the city that will lead you by some of Boston’s most iconic landmarks. Experience history firsthand as you walk by the Paul Revere House and the USS Constitution, and get a feel for the city as you discover shops, museums, and more historical sites along the way.

One of the best ways to experience Boston is by its many iconic breweries, including the original Samuel Adams Brewery . You can visit the brewery on your own and enjoy a meal and some drinks, or you can schedule a full tour of the historic facility. Even if you’re not a big beer drinker, it’s a fascinating experience to learn about the history of Boston and the brewery itself. Other well-known Boston breweries include Trillium Brewing , Harpoon Brewery , and Cambridge Brewing .

Speaking of Cambridge, a visit to Boston’s sister city is a must. Located just across the Charles River from Boston, Cambridge is notably home to Harvard University. The campus is known for its history and architecture, and visitors can enjoy a stroll through Harvard Yard , the oldest part of Harvard University. There are also a number of museums and shops throughout Cambridge, so you can truly enjoy the area for a full afternoon.

Catching a game at Fenway Park is an absolute must on any trip to Boston. Fenway Park is an iconic stadium and home to the Boston Red Sox baseball team. If you’re not able to watch a game at Fenway Park, another great option is to take a guided tour . You’ll be able to walk through various parts of the stadium and learn about its 100+ year history.

Not into sports? Grab a bite to eat and a drink at one of Boston’s many rooftop bars!

Day 2 in Boston

The perfect start to day 2 is a visit to Boston Common , a large park in the heart of the city, and the oldest city park in the United States. With beautiful landscaping and a number of landmarks dedicated to the park’s rich history, Boston Common is a great place to wander around and explore. Whether you like to run, bike, or just walk, Boston Common is sure to bring you a sense of relaxation.

If you’d prefer to spend your morning indoors, consider visiting one of Boston’s many museums. The Museum of Fine Arts is one of the best art museums in the world, while the Boston Tea Party Ships & Museum is an immersive experience perfect for history buffs.  

Afternoon Faneuil Hall Marketplace is the perfect afternoon destination to do some shopping and grab a bite to eat. The marketplace is home to a number of vendors who sell everything from clothing to souvenirs, books, and more. There are also a number of dining options in the marketplace that cater to all kinds of dietary preferences and restrictions. 

If you haven’t yet gotten your fill of shopping, a stroll down Newbury Street is a great way to spend an evening in Boston. Newbury Street, located in Boston’s Back Bay neighborhood, is well-known for its shops and restaurants.

The street is lined with historic townhomes that various retailers have come to occupy, and you’ll find everything from pop-up kiosks to high-end designer stores. Newbury Street is also a great place to find dinner and drinks after a full day of shopping. You can often find festivals and live music along the street, so make sure to check their website in advance to see a schedule of upcoming events. 

Day 3 in Boston:

Brattle Book Shop is a must-visit spot on any trip to Boston, and the perfect way to kick off day 3 of your adventures. The bookstore is one of the largest and oldest in America and contains a number of used books as well as a whole floor of rare publications. Brattle Book Shop is full of character and a great way to experience a slice of Boston culture. 

Spend your last afternoon in Boston exploring the city by air. Boston Helicopters is one of the most popular companies offering helicopter tours in the Boston area. They have a number of packages to choose from depending on specific sights you want to see, and you’ll be truly amazed by the opportunity to see a city from above. Taking a helicopter tour of Boston is a unique experience you’ll never forget, and a pretty epic way to close out your trip.

Time Out Market is an upscale food hall located in a massive venue with over 25,000 square feet of space to enjoy. Time Out Market is a unique dining experience that highlights some of the best food and drinks the city has to offer. There are more than 10 vendors inside the market that serve up everything from Italian, Mexican, seafood, and even gourmet pastries. If you’re an indecisive eater and like to have options, Time Out Market is the perfect spot for you. All the food is sure to be delicious, and you’ll remember your dining experience for months to come.

Other things to do in Boston

• Explore the Franklin Park Zoo ($19.95 for adults, $17.96 for seniors 62+, $13.95 for kids 2-12) 
• Keep your eyes peeled for whales and wildlife aboard this Whale Watching Cruise!
• Check out the city via trolley tour or historical boat cruise !
• Enjoy the unique architecture of the Hatch Shell , an outdoor concert venue
• Visit the beautiful I sabella Stewart Gardner Museum ($20 for adults, $18 for seniors, $13 for students)
• Take a guided scavenger hunt around Boston . You can choose from a haunted ghost tour, exploring murals, bar crawls, or several different hisotry tours.

Other tips to know before visiting Boston

The weather can often vary in Boston so you’ll definitely want to come prepared with layers. Comfortable walking shoes are also a must given all the adventuring you’ll be doing!  

3-day Boston Weekend Trip Itinerary Recap:

• Day 1:  Freedom Trail, Brewery Tour, Harvard, Fenway Park
• Day 2:  Boston Commons, Museums, Faneuil Hall Marketplace, Newbury Street
• Day 3:  Brattle Book Shop, Boston Helicopters, Time Out Market

One Weekend In Boston Isn’t Enough

As you can see, there’s SO much to do in Boston that one weekend would never be enough to see it all. You can customize your 3-day Boston itinerary based on what interests you. No matter what you’re looking for, you’ll find plenty of entertaining activities to create your own fun-filled, jam-packed adventure weekend in Boston!

What else would you add to this “One Weekend in Boston” Itinerary?

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Want an easier way to plan your Weekend Trips?! Click the picture below to download your FREE Weekend Getaway Planner!

Hey hey! I'm Jordan, a full-time elementary teacher with a side of freelance writing/travel blogging. As much as I LOVE to travel, I also enjoy routine, being home, and sleeping in my own cozy bed. Anyone else?  Enter...weekend getaways! I'm hoping you find this to be your one-stop-shop to plan your next USA weekend trip (with or without your pup).

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2 Days in Boston Itinerary: The Perfect Boston Weekend Getaway!

• April 23, 2023

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If you’re looking for an epic 2 days in Boston itinerary, you’ve come to the right place!

I freaking LOVED my time in Boston and, after almost a week spent sightseeing, eating and drinking there, I’m pretty confident that I’ve pulled together the best Boston weekend itinerary on the web (*hair toss*).

The city of Boston is surprisingly easy to travel around since it’s one of the few cities in the US with a comprehensive public transport system!

Pair that with its many captivating historical attractions , the mouth-watering Italian food and, of course, the fun accent (we love a fun accent!) and you’ve got the perfect recipe for an epic Boston weekend trip.

Planning a short trip to Boston can feel overwhelming, though. There are just so many things to do there! If it’s your first time in Boston it’ll feel even trickier.

Fear not – in this post, I’m going to cover all of the must-see attractions in the city as well as my tried-and-tested food recommendations. So, whether it’s your first time in Boston or your fifth, you’ll still find some solid recommendations in this itinerary.

Let’s get started!

Table of Contents

How Many Days Should I Spend in Boston?

Two days in Boston is the perfect amount of time to see Boston’s top sights, eat some incredible Bostonian food and get a flavour of the city.

It’s still possible to spend just one day in Boston, but you’ll have a very full day and will have to be very selective about what you add to your itinerary! For one day visits to Boston, I recommend sticking to the Freedom Trail walking tour.

For numerous reasons that I’ll go into down below, I actually ended up staying for almost a week in Boston! In my experience, this was a bit too long. However, if you’re able to extend your 2 days in Boston to 3 or 4 days you’ll get the chance to explore the city’s wonderful surroundings, such as Salem, Cambridge and Harvard, and Cape Cod!

So, in my opinion 2 days in Boston is the right amount of time to spend in the city itself. If you want to see any of the other nearby destinations you’ll need another day or two.

2 Days in Boston Itinerary: Step-by-Step

Here’s what to see in Boston in 2 days!

Day 1: The Freedom Trail and the North End

Stop 1: boston duck tour.

You’ll get the perfect introduction to Boston on the city’s famous duck tour ! This 80-minute guided tour takes you past all of the city’s highlights and gives you a whistle-stop tour of the city’s history and unique identity.

What makes the Boston duck tour so unique is that once on board you’ll get to check out the city from land and water . Yup! The duck tour takes place on a WW2-style amphibious vehicle , meaning you’ll get to whizz past all of the city’s most famous landmarks and cruise along the Charles River without moving from your seat!

Click here to book your seats in advance – this tour often sells out!

Stop 2: Walk the Charles River Esplanade

After an action-packed 80 minutes you’ll get dropped off near the Charles River Esplanade, so there’s no better way to unwind and check out one of Boston’s most scenic areas than by taking a riverside stroll. 

The esplanade stretches for three miles along the river, but obviously you don’t need to walk all of that!

Instead, I recommend just taking in a small chunk of it as you walk from the Duck Tour drop-off area towards Boston Common, the oldest public park in the United States.

Stop 3: Boston Public Gardens & Boston Common

Next up on this 2 day Boston itinerary is Boston Common, Boston’s version of New York’s Central Park.

You’ll get some beautiful views of the city’s skyline from here, and there are also plenty of fascinating places to visit inside the park.

Start in Boston Public Garden, where you’ll find the George Washington statue and a stunning suspension bridge over a lake where you won’t be able to resist taking photos. Heading over to the corner of the Boston Public Garden, you’ll find the adorable “Make Way for Ducklings” sculpture.

Locals often decorate the ducklings in custom-knitted outfits or hats, and children frequently sit on the back of the mother duckling for cute photos. It’s one of the most adorable sculptures you’ll ever see!

Walking over to Boston Common you’ll find plenty of different temporary attractions depending on the time of year you visit. I visited Boston over Memorial Day weekend so a huge part of the common was covered in American flags fluttering in the breeze, which was quite touching.

Stop 4: Lunch at Cafe 26

Fancy having breakfast for lunch? Great, because the popular Cafe 26 serves up exactly that.

This was the first place I ever tried banana pancakes , and wow they were worth the wait! The menu here is pretty huge, covering all of the classics, and the prices are reasonable. 

Stop 5: USS Constitution and USS Cassin Young

In the afternoon of your first day in Boston, I recommend heading over to the final few stops of the Freedom Trail. There’s a method to my madness here, I promise. The Freedom Trail has a lot of stops, and in my experience if you’re going to dedicate enough attention to each stop you can’t really do it in a day without being flat-out exhausted!

The parts of the Freedom Trail that are on the first day of this Boston itinerary are quite a walk away from all of the others, so it actually makes a lot of sense to split them up in this way.

USS Constitution

This famous ship from the War of Independence is still in the harbour over in Charlestown, and you’re able to board it and explore! Since it is located in Boston National Historic Park you’ll need a photo ID to enter . Luckily, though, admission is free !

As well as being famous for its exploits during the War of Independence, the USS Constitution is the US Navy’s oldest commissioned ship . It was built way back in 1797.

Wandering the decks and descending into the depths of the ship you’ll learn all about what life was like on board this ship for the crew who worked here, and you’ll be surprised by just how cramped it must have felt on board!

There’s not a whole lot of information on board, which makes it perfect for just roaming around, but if you’re looking for more history, check out the USS Constitution Museum next door.

USS Cassin Young

Just a short walk away and also inside the Boston National Historic Park (meaning entry to this ship is also free!) you’ll find the much more recent USS Cassin Young, which was built in 1943 .

This ship engaged in seven Pacific battles during WW2, survived two Kamikaze hits, and continued serving a whopping ten years past its expected retirement date!

You’ll only need 15 minutes here, making it an easy stop to squeeze into this whirlwind Boston 2 day itinerary, but if you’re at all interested in modern history it’s worth a quick walk around.

Stop 6: Bunker Hill Monument

Next up is the Bunker Hill Monument, the 221-foot stone monument which commemorates the Battle of Bunker Hill, which took place right here!

The Battle of Bunker Hill was one of the first major battles of the American Revolution. Although the park around the monument is a lovely place to hang out for a while, the reason we’re truly here is to climb to the top.

Yup, I hope you’ve brought good walking shoes because there are 294 steps to the top ! It goes without saying that from the top you’ll get epic views over Boston. What’s more, admission is free!

Stop 7: Drinks at Warren Tavern

It’s time to reward yourself after such a strenuous climb, and where better than the oldest tavern in Massachusetts? 

You’d think this impressive history would mean that it’s become a bit of a tourist trap, but I’m happy to confirm that isn’t the case! The service here is great, the food is delicious (so if you’re peckish I can recommend their pretzels and sweet potato fries ), and it has a lovely outdoor area where you can chill out in the sun.

The Warren Tavern has seen countless famous visitors over the years, including both George Washington and Paul Revere . If it was good enough for them, it’s good enough for me!

Stop 8: Boston’s North End 

It’s time to wrap up your first day in Boston in the North End, the city’s Italian quarter . It goes without saying that the food here is out of this world, and you really can’t go wrong!

If you’re visiting Boston for the weekend I highly recommend researching where you want to eat dinner and booking a table in advance . This is the hottest place in town for dinner, so you don’t want to miss out!

Mike’s Pastry and Modern Pastry

Start your visit in the North End at either Mike’s Pastry or Modern Pastry to sample their famous cannoli. Or even better – try them both !

There are some very strong opinions out there on whether Mike’s or Modern is best, but only you can decide for yourself. I personally preferred Mike’s, but I’d love to hear which one is your favourite!

Cannoli at both places costs $5 . Mike’s is where you head for exciting fillings and fun toppings, and Modern is where you head for authentic Italian cannoli. 

Caffè dello Sport

If you fancy checking out whatever sport is on at the moment, from basketball to European soccer, head to Caffè dello Sport. This community-feel cafe is the perfect place to grab a drink and catch the game in Boston.

Service is a little slow but it’s quite affordable and their Espresso Martinis are next level!

Carmelina’s

We dined at Carmelina’s and the food here was sooo tasty! I ordered the mushroom pasta and Rob ordered the gorgonzola pasta , and our first taste of American-Italian food did not disappoint!

Day 2: The Red Sox and Paul Revere

Stop 1: breakfast at tatte bakery.

Tatte is a Boston institution, and their baked goods take things to the next level! This Israeli-French coffee shop and bakery is awash with Instagram influencers thanks to its gorgeous decor and photo-worthy treats.

Even if you’re not an Instagrammer, though, it’s worth stopping here for breakfast. The food here tastes just as good as it looks!

Stop 2: Fenway Park

Even if you’re not into baseball you’ve probably heard of Fenway Park, home of the Red Sox since 1912 . Obviously the best way to see Fenway is at a Red Sox baseball game, but if there aren’t any fixtures during your time in Boston you have another option – to take a tour of Fenway Park .

This 1-hour guided Fenway Park tour will take you to all of the Park’s highlights such as the 37-foot tall “Green Monster” and the Red Sox Roof Deck, as well as the Fenway Park Living Museum where you can see some of the most famous Red Sox memorabilia in existence! 

Your guide will be able to answer any questions you have about Fenway Park and the Red Sox and will take you to all of the hotspots of the stadium.

Stop 3: Massachusetts State House

With Fenway Park ticked off your list, it’s time to complete the Freedom Trail by visiting the sites you didn’t get around to on day one of this Boston itinerary. Let’s start with the gold-domed Massachusetts State House , the state capitol. 

You can apparently go inside the building on free guided tours , but we decided to just check it out from the outside so I’m not sure how good the tours are.

The Massachusetts State House is in Beacon Hill, a beautiful neighbourhood. If you have time, it’s worth heading over to the historic and photogenic Acorn Street before carrying on.

Stop 4: Granary Burying Ground

A short walk around the corner is the Granary Burying Ground, which is the resting place of some of Boston’s most important historical figures and revolutionaries . In the cemetery, which was founded in 1660, you’ll find the graves of Paul Revere and Samuel Adams , to name just a few.

At the entrance to the cemetery there’s a guy handing out laminated guidebooks he created himself. You can borrow one for free , and I highly recommend picking one up. The guidebook will point out the most important graves, share a tonne of local history relevant to the graveyard, and point out a few lesser-known graves that are also interesting. 

There’s a wallet in the back of the guidebook where you can leave a tip if you wish before handing the book back as you leave.

Stop 5: Old South Meeting House and Old State House

Following the Freedom Trail, you’ll come across two of the most important buildings in Boston’s history – the Old South Meeting House and the Old State House.

Old South Meeting House

The Old South Meeting House was built in 1729 and was actually the place where the Boston Tea Party began. This is because it was the venue often used for big public debates about British rule as it was the largest public gathering place in Boston.

It was also outside this building that the protests over the Boston Massacre of 1770 took place. 

It’s totally fine to just check out this building from the outside (which is what I chose to do), but if you want to enter you’ll need to purchase the combined ticket. This ticket, which costs $15 , will get you entry to both the Old South Meeting House and the Old State House.

The Old State House 

The Old State House was built just before the Old South Meeting House, in 1713. It’s the oldest surviving public building in Boston and the front of the building was the 1770 Boston Massacre site .

It was also underneath the balcony of the Old State House that people gathered to hear the Declaration of Independence read out for the first time in 1776.

Afterwards, if you have time, head over to Faneuil Hall marketplace for a bit of shopping.

Stop 6: Lunch at Quincy Market

The historic Quincy Market is a must-visit in Boston if you want to sample some famous Boston cuisine . From clam chowder to lobster rolls, huge slices of Boston pizza to candy, this market has it all!

I can personally vouch for the hot butter lobster rolls at the Boston & Maine Fish Company (SO good!) and the pizza slices at Regina Pizza (the slices here are out of this world).

Stop 7: Paul Revere House

One of the most famous landmarks in Boston , and the top attraction on the Freedom Trail, is the Paul Revere House.

Whether you learnt all about Paul Revere in school or know absolutely nothing about him (and I was certainly in the latter category before my visit), the Paul Revere House is a fascinating place to visit where you’ll certainly learn a thing or two.

This black house was built around 1680 and was owned by Revolutionary figure Paul Revere from 1770 to 1800. He was living here when he embarked on his legendary “ midnight ride ” – and no worries if you have no idea what this is. You’ll find out all about it on your visit!

The Paul Revere House is open daily and tickets cost $6 for adults. Top tip: if you’re travelling alone you’ll need to pay in cash as they have a $10 card minimum here.

Stop 8: Old North Church

Just a short walk through the North End will lead you to Boston’s oldest church , the Old North Church. It was established in 1723 .

It costs $5 to enter, so I just decided to admire it from the outside. I’m from Europe, after all, so I’ve seen my fair share of old churches!

Aside from being so old, what makes the Old North Church so special? Well, it was from here that the infamous “one if by land, two if by sea” signal is thought to have been sent.

This was an early warning sign that the British Army was crossing the Charles River and heading towards Lexington and Concord on the night of Paul Revere’s Midnight Ride.

Stop 9: Drink at Green Dragon Tavern 

After such a jam-packed day of sightseeing, it’s time to reward yourself with a drink. There’s no better option than the historic Green Dragon Tavern .

The tavern was established in 1634 and played a key role in the War of Independence. It was apparently one of the favourite pubs of Paul Revere and John Hancock!

The decor on the outside and inside is so old and quaint, it felt like one of the old pubs at home in the UK rather than one in America! There’s a good range of beers local to New England here but you really can’t go wrong with Harpoon IPA.

Stop 10: Dinner at Rino’s Place

From the Green Dragon Tavern you’ll need to catch the T Blue Line from State to Airport station. The incredible Rino’s Place is just a short walk away and is absolutely worth the trip out to East Boston .

This family-run Italian restaurant has been featured on Diners, Drive-Ins and Dives . It also serves the BEST PASTA I HAVE EVER EATEN! Honestly, you guys, I would go back to Boston just to eat here again.

You can’t make reservations so if you’re visiting on a Friday or Saturday night you’ll have to wait for a table. If you get there early, though, you’ll probably walk right in. 

I ordered the lobster ravioli , which, at around $40 , definitely wasn’t cheap, but there was so much lobster stuffed into that ravioli that it probably should have been priced higher!

Rob ordered the matriciana, which I think was around $20, so much more affordable, but still mouth-wateringly good. The portion sizes here are insane so you’ll have to take your leftovers to go.

Extra Travel Information For Your 2 Days in Boston

Boston travel tips.

With 2 days in Boston you’ll have plenty of time to check out the city’s most famous attractions, sample some drool-worthy Boston food and leave you planning your next trip to return here!

I actually ended up staying in Boston for a whopping six days because I wanted to go at a leisurely pace (and see pretty much everything), explore the nearby areas, and catch the Paul McCartney concert at Fenway Park. It was one of the best things I have ever done!

Anyway, enough about me. If you’re looking for travel tips for your 2 days in Boston, here’s everything you’ll need to know.

Extending Your Weekend Trip to Boston

Got more time and fancy a long weekend in Boston? Great! Check out the Isabella Stewart Gardner Museum for awesome art, the site of the Old Corner Bookstore (which is now a Chipotle, lol), the Boston Public Library, or Park Street Church.

If you’re spending 3 days in Boston as a family, the New England Aquarium is the perfect place to visit on that third day.

If you’d prefer to get out of the city, there are also tonnes of brilliant day trips from Boston without a car that you can go on to explore some of the city’s surroundings. 

The easiest is probably Cambridge, where you can explore the famous Harvard and MIT universities. Another great option is Salem , Massachusetts. My Salem day trip guide will help you to figured this all out!

Fancy a trip to the coast? It’s possible to take the ferry from Boston to Provincetown, Cape Cod for a day trip, or head out on the train to Portland, Maine, amongst other great day trips!

If you do have the time, I highly recommend adding a day or two to your 2 days in Boston to give yourself some time to head out on a day trip or two.

Airport and Transportation Tips

The easiest way to get to Boston is to fly. Boston has one airport, Boston Logan International Airport (BOS) , and it’s pretty easy to get to the city from the airport. The easiest way is to catch an Uber , which will cost around $25 plus tip to downtown. 

However, you’re also able to catch the Blue Line of the T (Subway) . There’s a free shuttle bus from each airport terminal that will take you to the Airport subway station, and from here you can get downtown in around 30 minutes , which will cost you $2.40 .

You really don’t need to hire a car in Boston . It’s one of the best cities in the US when it comes to its public transport system! The main method of transportation you’ll use will be the T (what Bostonians call the subway).

The T has numerous lines all across the city and one-way tickets cost $2.40 . 

If you’re staying for two days or more in Boston and need to take the T from your hotel to downtown I recommend purchasing the 7-day pass for $22.50 . It works out as better value if you’re going to be taking the subway a lot.

What is the Best Time to Visit Boston?

I recommend visiting Boston in the shoulder season months of May, June, September, and October . Winters in Boston can be brutal, with short daylight hours. It’s best to avoid them if possible. Summers can also be baking hot in the city, which isn’t ideal for sightseeing.

It’s good to prepare for all types of weather during your 2 days in Boston. During my trip in early June I experienced torrential rain, extreme sun and heat, crazy humidity and one extremely windy day that was quite cold. Pack for all eventualities!

Where to Stay in Boston

Boston is expensive to visit, there’s no doubt. If you’re looking for a deal it’s better to visit Boston in winter, when hotel prices literally plummet. Weekdays are also, obviously, cheaper.

I’ve seen a hotel room on a summer weekend go for $500 when for a weekday in January it would cost just $150 – the price fluctuation is absolutely wild . If you’re visiting Boston on a weekend getaway, you’ve been warned! Book in advance!!!

It’s worth double-checking that there are no big events taking place in Boston for your dates before looking for hotels. 

We accidentally ended up in Boston on a night where both Paul McCartney played Fenway and the Celtics played in the NBA final at the TD Garden and… *shudders*… our accommodation for that night cost us SO. MUCH. MONEY.

Anyway, with that warning out of the way let’s get into some accommodation recommendations for your 2 days in Boston!

If you’re travelling to Boston on a budget, and especially if you’re travelling solo, this hostel is the best place to stay in Boston. Located near Boston Common , you can’t find a more central location! Breakfast is also included, which will help you to visit Boston on a budget.

Since this is the only decent hostel in Boston it gets booked up fast. I recommend booking as far in advance as you can. A dorm bed will set you back around $60 , so it’s certainly not cheap, but it’s by far the cheapest you’ll find in Boston!

Click here to check availability & book!

Budget Hotel

You guys, finding anywhere half-decent to stay in Boston on a budget is a mission, let me tell you. After putting my budget travel ninja skills to the test, the best I could find was this budget hotel , where we stayed for four nights.

You’ll have to catch the T for a couple of stops to get into the centre (the journey takes around 15 minutes), but it’s worth it for the money you’ll save. 

We paid $160 a night but split between the two of us it was $80 each, so not too bad. This is not the most incredible hotel you’ll ever visit but it’s clean, spacious, fairly affordable and it’s close to the T station. You don’t really need much more!

Click here to check availability & latest prices!

For the rest of my trip I stayed in this “budget” hotel , but I don’t have anything good to say about it aside from its location right next to the TD Garden. The rooms are tiny, it’s SO overpriced, and the staff sucked . 

Mid-Range Hotel

If you’re travelling to Boston on a mid-range budget your options open up when it comes to good-quality hotels in Boston! 

Word of warning for my European readers, though – a mid-range budget in the US typically costs more than double what you’d pay in Europe! Hotels in US cities are just expensive.

Situated just a 3-minute walk away from Boston Common, this boutique hotel is perfect if you’re looking to get something special from your fun weekend in Boston. You’ll feel super fancy entering its onsite cocktail bar, and you’ll love the sweeping views of the city from your hotel room window.

What Should You Not Miss in Boston?

Absolutely unmissable attractions in Boston are the Freedom Trail (especially the Paul Revere House), Fenway Park, Boston Common and the North End.

Is Boston Worth Visiting?

Yes! If you’re interested in history, or a foodie, you will absolutely adore Boston. Boston has an intricate and fascinating history, wonderful city views, some of the best food you’ll ever eat, AND it’s easy to navigate without a car! For this reason, I think it’s one of the best cities to visit in the USA.

Where Should I Stay in Boston to Walk Everywhere?

The best place to stay in Boston for first-timers, and people who want to walk everywhere, is Downtown, near the northern end of Boston Common.

How Long Does it Take to Walk the Freedom Trail in Boston?

If you were to simply walk the entire Freedom Trail without stopping, it would take you around 45 minutes. However, if you’re stopping to look around thoroughly at every attraction it could take over six hours! The average time it takes to walk the Freedom Trail and do some sightseeing is around 2.5 hours.

I absolutely adored my time in Boston and I’m certain that, by following this 2 days in Boston itinerary, you’ll have the time of your life here too!

I’d return to Boston in a heartbeat, even after I spent six days there!

I’ve tried to cram as much as possible into this Boston trip, but the more time you spend in the city the more you’ll get to see. There are just so many things to do in Boston!

If you’re waiting for a sign to visit Boston this is it. Go! You can thank me later 🙂

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Ella Moore is the founder of Many More Maps. Growing up just 45 minutes away from Liverpool, Ella has spent years exploring the city inside out. In her teenage years, she was introduced to the music of The Beatles, and the rest, they say, is history! Today, she stands as a leading authority on Beatles tourism in Liverpool, helping over 40,000 people a month to plan their dream trip to the city.

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Hi thanks for the articles..I’m taking notes. I will be visiting for the first time in September …I have a full busy schedule planned with several day trip tours BUT I have not been able to find a way to get to Vermont without a car. I don’t want to rent a car. I haven’t been able to find a feasible way to get there. I have googled and searched for train or bus routes but no luck. I would appreciate it if you have any advice. I am looking for a day trip. Thanks

Hi Norma – thanks for your lovely comment! I had the same problem looking for connections to Vermont. I think the realistic answer would be that it’s not possible to do a day trip to Vermont without a car – though I would love to be proven wrong! Your best bet is probably to fly there and spend a few days. There are direct flights from Boston to Rutland, VT. Have a great trip!

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Home » North America » Boston

WEEKEND in Boston – 48 Hour Guide (2024)

Located in the US state of Massachusetts, Boston is one of New England’s most picturesque waterfront cities. This modern metropolis still retains its old-worlde charm, and the whole city tells tales of its history and significance in American culture.

Boston is loaded with sights and attractions that’ll make you feel like you’ve stepped into a time machine! However, you don’t have to be a history-lover to enjoy this city. Boston has a vibrant nightlife scene, out-of-this-world cuisine and plenty of outdoor activities that will make your trip to this charming New England city as memorable as possible!

Boston is the perfect place to take your next vacation. It has a compact city center, loads of tourist attractions, and easy to use public transportation that’ll make your trip leisurely yet eventful!

If you’re looking for things to do in Boston this weekend, check out this helpful guide that’ll ensure you make the most of your weekend getaway!

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Insider Tips for an AMAZING Weekend in Boston

Boston nightlife guide, boston food guide, sporting events in boston, weekend cultural entertainment in boston – music/concerts/theatre, boston weekend travel faqs.

2 days in Boston will give you plenty of time to explore this historic city, but the key to spending your weekend wisely is staying in central Boston ! This will mean you save travel time and costs moving between the various things to do.

Know Where to Stay in Boston

Boston has many accommodation options to choose from, with prices to suit all budgets!  

Whether you’re looking for a friendly Boston hostel , a budget hotel, or a lavish 5-star room, you’ll want to make sure the location is near to the main attractions, so your Boston itinerary is as accessible as possible!

Our Favorite Hostel – HI Boston

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• Male, female and co-ed dorm rooms available
• Clean, comfortable and modern
• Free breakfast and WIFI

HI Boston is centrally located next to most of the city’s top attractions, including Boston Common and Chinatown. There is also a subway stop within walking distance. This hostel has a large community kitchen and lounge area where guests can socialize.

Our Favorite Airbnb – Studio in Prime Location

• Spack dab in the heart of Back bay is this astonishing home that offers one of the most comfortable stays in the city. It’s definitely one of the best Airbnbs in Boston .
• Located on the lively street of Newberry, you have access to the most premier shopping in the city and the award-winning restaurants you’ve only seen on tv.
• Speaking of food, the kitchen is small but does have everything you need to cook a quick meal, but being in the popping neighborhood, you will most likely be enjoying all the cafes he neighborhood has to offer anyways.

Our Favorite Budget Hotel – Boston Hotel Buckminster

• Close to Fenway Park and public transportation
• On-site dining and fitness center
• Microwave and refrigerator in every room

The Boston Hotel Buckminster is located in a great area of Boston. You’ll be within walking distance to many of the city’s top attractions as well as restaurants, bars, and shops. This historic building is well maintained and includes all modern amenities.

Our Favorite Splurge Hotel – Boston Park Plaza

• Restaurant on-site and room service available
• Two fitness facilities offering personal training and group fitness classes
• Every room has a coffee machine

Located in the heart of Boston, this lavish hotel has it all! The rooms are large and spacious and equipped with a flat-screen TV, black out shades, a refrigerator, and more! All rooms also include city views!

Know How to Get Around in Boston

Boston is one of the easiest cities in New England to get around. There are a few different options for transportation around the city, the main forms being the subway, bus, and on foot.

Driving can be a bit of a challenge if you’re unfamiliar with the city. If you decide to drive then be prepared to navigate old and outdated roadways and pay a stiff price for parking.

Taxi’s and ride-sharing apps such as Uber and Lyft are great options for quick and reliable transportation. Your driver will be more familiar with the layout of the city and you won’t have to pay parking fees!

The Massachusetts Bay Transportation Authority, or MBTA is Boston’s public transportation system. The subway is the most popular form of public transportation and is identifiable by a large “T.” The bus, commuter rail, and ferry are other options for transportation around Boston.

To ride the MBTA you must purchase a paper ticket called a “Charlie Ticket,” or a plastic card, called a “Charlie Card.” These can be purchased at electronic fare vending machines, at various local stores and select T stations.

Boston is a compact city and all of the main tourist attractions are within pedestrian friendly walking zones. All you need is a map and a good pair of walking shoes! For more info, visit our awesome Boston Travel Guide.

Save more and experience more. Get a city pass before you travel.

Weekends in Boston are the ideal time to experience the nightlife. Different areas of the city have different options for going out.

Here are the best districts in Boston to experience the vibrant nightlife!

Theatre District

• From late-night clubs, to casual wine bars, there’s something for everyone!
• Prices to suit all budgets – inexpensive to high-end
• Easily accessible by public transportation

You can’t go wrong going out in the Theatre District! This area of the city has nightlife options for everyone. The Tam is one of the best dive bars in the city, it has a laid-back vibe, casual atmosphere and affordable prices. Or, check out Stoddard’s Fine Food & Ale for vintage cocktails and craft beer in a historic setting.

Central Square

• Known for its wide variety of ethnic restaurants, live music venues, and bars
• Up-and-coming area of Boston
• Different options to suit everyone’s preference

Central Square is a neighborhood in East Boston. It has an eclectic range of nightlife options. Check out the Middle East Restaurant and Nightclub for an eventful evening. This club combines Middle Eastern cuisine with Boston’s rock and roll music scene. You’ll find at least one performance every night of the week!>

Fenway Park

• Sports bars, dance clubs, live music venues, eateries, and more
• One of the most lively areas to enjoy your Boston weekends
• Concentration of nightlife options are centered around Lansdowne Street

Fenway Park is an area of the city where Boston’s sports culture and nightlife thrives. It doesn’t have to be game-day to draw a crowd, this area stays busy year-round. Check out Lucky Strike for 3-stories of fun; this venue features a bowling alley, dance floors, lounge area, and more!

Food is an integral part of any holiday getaway! If you’re exploring Boston in 2 days, here are a few options to check out to experience the local food culture!

Best Dining Experience – The Union Oyster House

• The best restaurant in the city for seafood lovers
• Built in 1771 and turned into a restaurant in 1826
• Enjoy Boston specialities like New England clam chowder and Boston baked beans

The Union Oyster House is one of the oldest restaurants in the United States, and registered as a National Historic Landmark. This historic eatery serves classic New England seafood specialities. It has hosted famous patrons across the decades, including Presidents, actors and authors. Mix history with dining for the ultimate Boston culinary experience!

For a Social Dining Experience – The Q

• Simmering pot of soup stock with a variety of raw east Asian ingredients you prepare at the table yourself!
• Chinese cooking method that allows for family-style dining
• Great for a casual and social dining experience

In a manner similar to fondue, you grab and dip your food into a hotpot of freshly made broth. The pot is kept simmering in the middle of the table while everyone cooks their favorite raw ingredients, just the way they like them! Choose your favorite broth flavor and your favorite ingredients, including veggies, seafood, and meat.

The Best Market – Boston Public Market

• A great way to sample the local culinary flavors of Boston
• Indoor, year-round market, open everyday
• Casual style eating, great for groups and people with different dietary needs

Boston Public Market has a large and diverse variety of local food and drink options. From snacks, to mains, to dessert, to drinks, there’s something for everyone! The atmosphere is hip and trendy and all of the food and products are made locally. To check out what the locals eat, make sure to include this in your Boston weekend trip!

If you have time, you could even take one of the many fantastic food tours in Boston !

A Boston weekend trip is the perfect time to experience the city’s sports culture. Here are a few of our favorite activities to enjoy on your weekend away.

Watch the Red Sox at Fenway Park

• One of America’s most beloved ballparks
• Watch a match and immerse yourself in the electric feel of game-day
• The oldest ballpark in Major League Baseball

Bostonians are loyal Red Sox fans, and a trip to Fenway Park is a must see attraction for sports enthusiasts! If your Boston weekend coincides with a home-match, watch a game and experience the local sports culture. Game-day is sure to bring high energy and a lively atmosphere! Can’t catch a game? Tours of the stadium are also available year-round

Stretch Your Legs at Millennium Park

• A great place to get some exercise and fun for all ages
• Enjoy scenic views of the Blue Hills, Newton’s hills, and downtown Boston
• Picnic tables, playground, toilet facilities and lots of parking

Millennium Park is an outdoor oasis located on the outskirts of Boston. Enjoy 6-miles of accessible trails, large grassy fields, a canoe launch and gorgeous views. There’s enough space for everyone to partake in whatever outdoor activity they enjoy. Go for a run, walk your dog, fly a kite, or kick around a soccer ball.

Canoe or Kayak the Charles River

• A different way to experience the city and get a bit of exercise
• A great activity for outdoor enthusiasts spending two days in Boston
• Fun for all ages and skill levels and perfect for the whole family

Enjoy breathtaking views of Boston’s skyline while experiencing the tranquility of floating on water. Escape the hustle and bustle of the city and head out on the water for a relaxing reprieve. Have a leisurely paddle by yourself, or book a tour and journey along with others as you enjoy a panoramic sea view of the city!

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>A weekend trip to Boston will give you plenty of time to explore the city’s music and theatre culture. Add a stop at one of these venues to your Boston in 2 days itinerary for an entertaining experience.

Boston Opera House

• Hosts popular broadway shows, musicals, ballet performances, and concerts
• Wonderful selection of performances, amazing acoustics and good visibility
• Open and operating since October of 1928

The Boston Opera House is the best place to go in the city to experience the city’s performing arts culture. This grand theatre is designed in a combination of French and Italian styles. It is wonderfully decorated with ornate detail and is a piece of art in its own right.

House of Blues Boston

• Friendly vibe and casual aesthetic
• Diverse selection of live music, from bluegrass to techno
• Rock- and blues-themed chain

Enjoy dinner and a show at the House of Blues in Boston. This Boston attraction makes for an entertaining night out. The venue is the perfect size, small enough to allow for a more personalized experience, but big enough to experience the music culture with others. Their menu features southern staples and classic American dishes.

Wilbur Theater

• Historic performing arts theater that originally opened in 1915
• Features basic concessions and a full bar
• Comedy and music venue

The Wilbur Theater is located in the heart of Boston’s historic theater district. The capacity of the theater is 1,200, making it a smaller sized venue, which allows for great views from every seat and a more personal show experience. You’ll find A-list talent performing here, with past acts including Joel McHale, Jimmy Fallon and Bill Maher!

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10 Other Awesome Things to do in Boston This Weekend

If you’re in Boston for a weekend here are a few more places we recommend checking out that’ll make your weekend as eventful as possible!

#1 – Explore Boston’s Museum of Fine Arts

The Museum of Fine Arts in Boston is the fifth largest museum in the United States. It has a comprehensive collection of more than 450,000 works of art. Peruse the museum and enjoy art collections for the Americas, Africa, Asia, Europe, and more!

Check out the “Garden of the Heart of Heaven,” a peaceful and picturesque Japanese garden. Walk around more than seventy species of plants and enjoy the meditative atmosphere. You could easily spend all day here, so if you’re spending 3 days in Boston or more, make sure to take your time exploring all the areas that interest you.

#2 – Wander Around Beautiful Beacon Hill

Beacon Hill is the area of Boston you see on postcards. With red brick mansions, cobblestones paths, gas street lamps, and tree-lined streets, Beacon Hill is a must-see area of the city. This historic district is filled with boutique shops, casual eateries, and cozy coffee shops.

Enjoy a peaceful stroll and admire the upscale Bostonian living. Make sure to check out Acorn Street, it is one of the most photogenic spots in Boston. This historic street is one of the very few streets in the U.S. with its original cobblestones still in place. You’ll feel like you’re stepping back into colonial times with a trip to this iconic Boston site.

#3 – Walk Along the Freedom Trail

Freedom Trail is a 2.5-mile-long path that winds through downtown Boston. It covers 16 locations significant to the history of the United States and is one of the most popular attractions in the city.

Follow the red line on the sidewalk to take your own self-guided tour of important American Revolution sites . The trail starts at the Boston Common, a large public park, and ends at the iconic Bunker Hill Monument.

#4 – Visit the Boston Tea Party Ships and Museum

Boston is one of the most important cities in American History . Relive the most important events leading up to the American Revolution at the Boston Tea Party Museum. Engage in interactive and informative exhibits alongside a fun cast of actors. This museum operates a little differently than other museums.

For 1-hour you’ll be guided by an 18th-century costumed host on a fully immersive tour. You’ll visit the ships and museum, watch a multi-sensory documentary, experience an interactive town meeting, and get a chance to dump tea bags into the harbor! This museum is designed to engage all ages and is fun for the whole family!

Book your Boston Tea Party tickets here !

HI Boston is centrally located next to most of the city’s top attractions, including Boston Common and Chinatown.

• Free Breakfast

#5 – Relax at The Boston Public Garden and Boston Common

The Boston Public Garden is a large park nestled in the heart of the city. It was the first public botanical garden in the United States. Enjoy the lush Boston landscape and the social ambiance at this serene section of the city

Adjacent to this park is the Boston Common. We thought we’d include both areas, seeing as they’re directly next to each other and can easily be visited in one trip. The Boston Common is the oldest city park in the United States, dating from 1634!

This area of the city is a great place to recharge before continuing your weekend in Boston itinerary!

#6 – Step Back in Time with a Trip to the Paul Revere House

Built in 1680, the Paul Revere House is the oldest remaining building in downtown Boston. It belonged to American patriot, Paul Revere during the time of the American Revolution. This original 3-story house operates as a non-profit museum. For a small fee, guests can tour the house at their own pace.

This self-guided tour takes you through the life of the Revere family, Paul’s trade, and his involvement in the American Revolution. There is also an education and visitor center connected to the house for further learning. For history-lovers trying to decide what to see in Boston in 2 days, this stop is a must-see attraction!

#7 – Visit the Gravesites of Famous Americans at Granary Burying Ground>

Filled with history, the Granary Burying Ground is Boston’s third-oldest cemetery, founded in 1660. This cemetery holds an estimated 5,000 people, including famous Bostonians and early Americans.

The most famous gravestones belong to Paul Revere, Samuel Adams, and John Hancock. Five victims of the Boston Massacre are also buried here as well as Benjamin Franklin’s parents. This cemetery sits quietly in the middle of the city, surrounded by tall buildings and busy streets. It’s located along the Freedom Trail and is free to enter.

#8 – Take a Boston Brewery Tour

Boston is famous for its craft beer scene, what better way to experience the local beer culture than on a brewery tour! There are several brewery tours in the city to choose from, but we recommend Harpoon Brewery and Beer Hall.

This brewery is located in Boston’s Seaport District and is the perfect place to enjoy beer with friends! Learn about the brewing process in Boston and enjoy a range of freshly-brewed Harpoon beers. This brewery is also well known for its large pretzels, which are made on site from the leftover yeast of beer brewing! Pair a pretzel with your pint at this fun Boston brewery!

#9 – Visit North End

North End is Boston’s oldest neighborhood. This area of the city is also referred to as Boston’s Little Italy. Here you’ll find narrow streets lined with some of the city’s oldest buildings, and of course, lots of Italian restaurants and pastry shops!

The Freedom Trail passes this area of the city. This is the location where the famous “one if by land, and two if by sea,” signal was given to Paul Revere that launched his midnight ride (“The Redcoats are coming!”) , and thus, the American Revolution! Walk the cobblestoned streets, admire the architecture, and take in the delicious aroma of Italian food!

#10 – Enjoy Some Fun in the Sun at The Lawn on D

The Lawn on D is an outdoor playland that’s fun for all ages! This Boston attraction is always buzzing with energy and a fun social atmosphere. There are large circular swings, lawn games, life-size checkers and chess sets, live music, and more!

This social hangout is a great place to meet new people. There are a wide variety of food trucks where you can enjoy a bite to eat, or grab a cold drink and relax on the lawn. Adults and kids will both enjoy this addition to their Boston weekend getaway.

Now that we’ve covered the Boston places to visit , we thought we’d add in a few more details about the city and answers to questions you might be asking yourself.

Here are some of the most frequently asked questions.

What should I pack for a weekend in Boston?

– Walking Shoes  – Boston is a compact and walkable city, and It’s entirely possible to spend all day on your feet. Some areas of the city are still paved with cobblestones which means your walking surface will be uneven. A comfortable pair of sneakers with good support will be your best friend when walking around Boston in two days! – Jacket –  Boston’s weather leans towards the cooler side. Even in summer, night-time temperatures can get quite chilly. The weather can easily change from one day to the next and its best to be prepared for whatever temperatures you might experience. Rainfall is also common in Boston throughout the year. – Bag –  Boston is a city that will keep you moving, and it’s very possible to spend your whole day out exploring. A good  quality daypack  can easily store all of your “extras.” Whether that be hats, sunscreen, a jacket, an umbrella, or your camera. It’s also a great place to store any Boston souvenirs you pick up!

Can I get an apartment in Boston for the weekend?

Booking an apartment in Boston for the weekend has never been easier! You’ll have a couple of options to choose from when selecting your accommodation. Airbnb is widely used by tourists visiting Boston. This is a great choice for groups in particular, as splitting the cost of your accommodation more ways will help save you money. Airbnb apartments are usually booked out through locals, meaning you’ll get a real local Boston experience when you select this form of accommodation. Another way to find an apartment in Boston is by checking  booking.com . This popular online platform provides all sort of accommodation options, including apartments. Just switch your search to the “apartment” option when filtering accommodation options, and you’ll be shown a list of apartments in Boston. This can be a great option as apartments tend to have more amenities than hotels and hostels. These usually include a kitchen, laundry facilities, living area, and more space in general.

Is Boston safe for a weekend trip?

Whether you’re exploring Boston in 3 days, or more, safety is an important thing to keep in mind. Boston is considered a safe city to visit, however, as with any other major city, there are certain  safety precautions when traveling  you’ll want to take. It is not recommended to visit the Boston Common or the Public Garden after the sun goes down, unless you are there for a public event, such as a concert. The North End, the Waterfront area, and the Theater District are typically full of people and stay busy, but you should be cautious very late at night as well. Pickpockets or bag and purse snatching is common in tourist areas and public transportation. Remain vigilant, keep your valuables close to you, and never leave your items unattended. Stay in well-populated areas, travel with others when possible, especially at night, and keep track of your belongings. Following these simple guidelines and you should be just fine!

Don’t Forget Your Boston Travel Insurance

ALWAYS sort out your backpacker insurance before your trip. There’s plenty to choose from in that department, but a good place to start is Safety Wing .

They offer month-to-month payments, no lock-in contracts, and require absolutely no itineraries: that’s the exact kind of insurance long-term travellers and digital nomads need.

SafetyWing is cheap, easy, and admin-free: just sign up lickety-split so you can get back to it!

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Final Thoughts on a Great Weekend in Boston

Boston is one of the oldest and most historic cities in the United States. Weekends are a great time to experience this city in high-drive! Whether you’re a nature-lover, history-buff, food fan, beer drinker, or sports enthusiast, you’ll find options to suit everyone’s preferences.

As one of New England’s most vibrant and scenic cities, countless visitors are drawn to Boston each year. It has all the components necessary to make for a memorable trip and is a city you’ll want to keep coming back to!

We hope this guide has helped you discover all the highlights of this east coast city. From its early American architecture to its rich culture to its charming scenery, you’ll find it all in Boston!

Made it this far? You get 15% OFF to book a place to stay ! Offer valid exclusively for Broke Backpackers 😉

Mary Beth Skylis

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How to spend the perfect weekend in Boston

Jul 3, 2019 • 4 min read

Boston, Massachusetts, USA skyline at the public garden.

Whether you come for the US revolutionary history, the esteemed institutions of higher education or a tasty lobster roll, spending a perfect weekend in Boston is always within reach.

Begin your explorations at Boston Common , an intersection of neighborhoods both contemporary and historic. The Massachusetts State House towers over the Common from the northeast corner; fountains and statues dot the park; and Bostonians bustle to and fro. From here, it’s a one-mile walk to your dining destination, following the Freedom Trail .

This red-brick path passes some of the landmarks of the colonists’ fight for independence from the British crown. Look for the Granary Burying Ground , the final resting place of many revolutionary heroes; the Old South Meeting House , where rabble-rousers instigated the Boston Tea Party; and the Old State House , site of the 'Boston Massacre,' the first violent skirmish of the revolution. Faneuil Hall is the 18th-century meeting and market place that is now the center of Boston tourism action.

Stroll across the North End Park and into the eponymous neighborhood, where the sounds and scents of Italy drift through the doorways. Boston’s Italian heritage will tantalize your senses as you wander through the streets crammed with restaurants, bakeries and cafes. Join the line for an affordable feast at Giacomo’s Ristorante or make a reservation for an intimate affair at Pomodoro . The grand finale is cannoli from Modern Pastry Shop .

Rise and shine and learn the best way to see Boston is on two wheels. Rent a bicycle at  Urban Adventours or  Blue Bikes . Pedal along the Charles River Esplanade for flowering trees and shady paths. Or cross to the north side of the river (Cambridge) for city views and academic ambiance. Along the Charles River Bike Path , it’s about 5 miles one way to Harvard Square.

You’ll ride past the Massachusetts Institute of Technology  (MIT), where you can stop to tour the campus’s impressive collection of modern architecture and public art. Or, continue two miles west to Harvard Square to explore the original Ivy League institution , not to mention the bookstores, record shops, clubs and cafes that fill the streets around it.  The options for refreshment are plentiful, including Café Pamplona in Harvard Sq and Roxy’s Grilled Cheese near MIT.

Head back downtown in time to hop on a New England Aquarium Whale Watch (last boat leaves at noon, 2:30pm or 5:30pm depending on the season; reserve in advance). Feel the ocean breeze and enjoy the scenery as you journey out to Stellwagen Bank , a rich feeding ground for marine mammals and birds. Onboard naturalists point out humpbacks, finbacks, minkes, pilot whales and right whales, as well as dolphins, sharks and more. Whale sightings are guaranteed.

Debarking from the cruise at Central Wharf, you’re perfectly placed for a stroll along the Rose Kennedy Greenway , a strip of manicured parkland that snakes through downtown Boston. Take a ride on the Carousel , cool off in the Rings Fountain and admire the lush gardens and eclectic art, as you make your way to the Seaport District.

This seaside neighborhood was the old fishing district, centered on gritty Fisherman’s Wharf. It’s been snazzied-up in recent years, but it’s still the best place to sample the city’s freshest seafood. Here’s your chance to slurp some oysters, savor some chowder or devour a lobster roll. You’ll find a myriad of options for waterfront dining or rooftop drinking; we like Legal Harborside or Barking Crab for the former, Lookout Rooftop Bar or Trillium Fort Point for the latter. The wonderful views of the Boston Harbor and city skyline are hard to beat.

Reserve a table for Sunday jazz brunch at the Beehive . Feast on decadent food like eggs shakshuka (poached eggs with tomatoes, peppers and spices). Sip a concoction from the Bellini bar. And enjoy music courtesy of faculty and students from the local Berklee School of Music.

After brunch, stroll through the South End, admiring the Victorian row houses and English gardens.  South of Washington St, residential changes to post-industrial. Now known as SoWa, this is Boston’s vibrant art district, crammed with studios and galleries and – on Sundays – a giant art market. SoWa Open Market is the city’s largest gathering place for makers of all types, and you’ll find everything from handmade jewelry and designer clothing to artisanal soaps and pottery. Just in time for you to pick up a one-of-a-kind souvenir to remember your weekend in quirky, creative Boston.

Where to Stay

The Revolution Hotel offers a new concept in affordable lodging. The guest rooms are small but fresh, and furnished with fluffy pillows, quality linens and high-tech gadgetry. Shared bathrooms are spotless, and well stocked with plush towels and high-end toiletries. (En suite bathrooms are also available.) Art-filled common spaces and the South End location make this place a fantastic option for the budget-conscious traveler.

Alternatively, go upscale at No 284 , a boutique hotel housed in a Back Bay brownstone. Luxurious amenities, original art and contemporary design are perfect complements to this classy location on Commonwealth Ave.

How to get there

Logan International Airport is 15 to 20 minutes away from downtown Boston. The free Silver Line bus takes passengers to South Station, from where the T (Boston’s metro system, $2.40 to $2.90) goes almost anywhere in Boston. Alternatively, a free airport shuttle bus takes passengers to the Airport T-station.

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• 21 free things to do in Boston

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Boston   Travel Guide

30 Top-Rated Things to Do in Boston

As Massachusetts' capital and the birthplace of the American Revolution, there's no shortage of historical sites for travelers to explore within Boston's city limits (and beyond). There's even a Boston Tea Party Museum on the harbor

• All Things To Do
• 1-Day Itinerary
• 2-Day Itinerary
• 3-Day Itinerary

Freedom Trail Freedom Trail free

Stretching 2½ miles, the Freedom Trail weaves past 16 of the city's most historic sites, including Faneuil Hall Marketplace , the Paul Revere House and Old North Church . Taking in all of the trail's attractions requires at least half a day (and some comfortable walking shoes), but you can easily plot points of interest before you begin your jaunt from Boston Common .

Though most visitors agree the trail is easy to navigate on your own, some recommend a guided tour or downloading an app to tell you about the sites. (You'll find a handful of apps available for Apple and Android devices.) If you have a Go Boston Card, standard guided tours given by the Freedom Trail Foundation are covered by your pass.

Faneuil Hall Marketplace and Quincy Market Faneuil Hall Marketplace and Quincy Market free

U.S. News Insider Tip: Every Friday and Saturday, Haymarket (one America's oldest open-air markets) pops up adjacent to Faneuil Hall. In order to navigate this often-chaotic scene successfully make sure to bring small bills, leave bulky bags at the hotel and keep it moving on the sidewalk. - Jill LeGrow

Four buildings – Faneuil Hall, Quincy Market, North Market and South Market – constitute Faneuil Hall Marketplace, with the oldest being Faneuil Hall. Built in 1742 and now a stop on the Freedom Trail , Faneuil Hall has had a long and important history in Massachusetts politics. Samuel Adams once stood here to push for resistance against the British, and abolitionists and suffragists have stood on their soapboxes here. In fact, this is where colonists famously challenged the Stamp Act of 1764 by proclaiming, "no taxation without representation." From those illustrious days, the marketplace has expanded to include more than 100 shops and restaurants.

Boston Public Garden Boston Public Garden free

Though the Boston Public Garden sits right next to Boston Common , the two are quite different. The public garden is newer (established in 1837) and holds the distinction of being America's first public botanical garden. Flowers and trees are beautifully organized and kept in quality condition throughout. You can see the colorful arrangements and exotic trees from the 6-acre pond as you glide along the water in a Swan Boat. Additionally, the park houses two of Boston's most iconic statues: Make Way for Ducklings (a bronze sculpture of a duck and her eight ducklings) and a sculpture of George Washington (which shows America's first president riding on a horse).

Visitors looking to relax after sightseeing will enjoy the Boston Public Garden. Parkgoers say you'll find plenty of shade beneath the park's trees, which comes in handy on hot summer days. Plus, you'll likely spot some ducks and geese swimming around the lagoon. And if you have a few dollars, visitors recommend taking a 15-minute ride on a Swan Boat. The large paddle boats cost $4.50 to ride (or $3 for kids ages 2 to 15 and $4 for seniors); travelers with Go Boston Cards ride for free. Swan Boats are usually available between mid-April and Labor Day.

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North End North End free

Chances are you'll end up in the North End at least once during your visit to Boston. It's steeped in the city's rich history as it holds the title of Boston's oldest neighborhood and houses three attractions on the Freedom Trail . What makes this neighborhood a top point of interest, however, is its Italian culture: The North End is considered Boston's Little Italy.

While Italians weren't the first to settle in this area (English settlers arrived first then European Jews, African Americans and Irish immigrants), their cultural influence on the North End withstood the test of time. Today, you'll find all kinds of Italian food from classic pizza pies served at the popular Regina Pizzeria to Sicilian-style seafood, such as black linguine (made with squid ink) and calamari meatballs at The Daily Catch . For dinner, try Mamma Maria for fine dining, Giacomo's for its affordable, made-in-house pasta or Bricco , which sources its meats and bread from its own meat and bread shop, located right next door. If you’re only interested in pizza, hit up Galleria Umberto for delectable solo slices or Antico Forno for its full-size, wood-fired pies. Prezza is known for its extensive wine list, boasting hundreds of wine labels to choose from. For dessert, make sure to pick up a cannoli at Mike's Pastry or Modern Pastry , or tiramisu at the 24-hour Bova's Bakery .

Museum of Fine Arts Museum of Fine Arts

If you want to make the most out of the Museum of Fine Arts, one of the most comprehensive art institutions in the country, then you'll need to spend a good chunk of your day here. The museum is home to one of the best art collections in the world, including the celebrated Art of the Americas wing. Inside this sprawling collection, you'll encounter galleries showcasing iconic pieces from indigenous cultures in North, South and Central America to works by contemporary artists like Edward Hopper.

You'll also find an impressive collection of Asian art here, plus works from Monet, Renoir, Manet and Rembrandt on display. And in special temporary exhibits, you can admire masterpieces from Black artists like Diedrick Brackens and Picasso, among others.

Boston Common Boston Common free

The grounds of Boston Common started as a cow pasture in the mid-1600s. It was also used for Puritan punishments, like whipping, and even for hangings. In 1768, the area was transformed into a British camp. After the Revolutionary War, the park became a popular locale for public speeches and rallies. Now, the Common is best known because of its status as the oldest public park in the country. You'll also find a variety of activities and events – including theater and musical performances and free fitness classes – hosted here throughout the year. If you plan to traverse the Freedom Trail , you'll start the walk here at Boston Common.

Though some visitors say you won't find much to do in this park, Boston Common is great for picnics or a leisurely stroll. Travelers also mention that this site is a wonderful spot to take young children. In addition to ample running room on the park's green space, kids can play at the Tadpole Playground or Frog Pond. Frog Pond offers a spray pool during the warmer months and an ice skating rink in the winter. Some visitors do note that the park tends to draw Boston's homeless population, particularly at night.

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Fenway Park Fenway Park

U.S. News Insider Tip: If you want to watch a Sox game without a ticket, head to the Bleacher Bar on Lansdowne Street. Located beneath the bleachers of Fenway, the best tables are positioned directly in front of the huge garage window that overlook centerfield. – Jill LeGrow

Fans of America's favorite pastime won't want to miss a game at Fenway Park. Home to the Boston Red Sox, this stadium has been the site of home runs, stolen bases and grounders since 1912. Regardless of whether or not you're a diehard Red Sox fan, you should try to catch a game and admire the ballpark's original architecture. Must-see features of the park include Pesky's Pole – the right field foul pole named after former Red Sox player Johnny Pesky – and the 37-foot-tall "Green Monster" wall in left field.

Isabella Stewart Gardner Museum Isabella Stewart Gardner Museum

After Isabella Stewart Gardner's husband died in 1898, the art enthusiast carried out their plan to buy land in Boston's Fenway area and open a museum to display her impressive collection of Italian art. The museum, which was fashioned after the Palazzo Barbaro in Venice , was completed in 1901, at which point Gardner moved in to the fourth floor and began installing her collection. Today, you can visit this Boston museum to get your fill of the Italian masters, such as Raphael and Titian. The building also showcases a cache of beautiful furniture, photographs, sculpture and rare books straight from Europe. The museum's New Wing, designed by Renzo Piano, includes a glass atrium, greenhouses and landscaped gardens.

The art isn't the only interesting thing here: the museum is also the site of the single largest property theft on Earth. In the wee hours of March 18, 1990, two thieves made their way into the museum disguised as police. The duo stole 13 works, including pieces by Rembrandt, Vermeer, Degas and Manet. Today, the museum has empty frames on the walls as placeholders until the art returns to the museum. As you may have guessed, the crime has not been solved and the works haven't been recovered. The museum is even offering a sizable reward ($10 million) for information leading to the art. 

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Boston Public Library Boston Public Library free

A library isn't always all about books. The main branch of the Boston Public Library in Copley Square, which opened in 1895, is so much more, according to recent visitors who call the architecture "beautiful" and a “must-see.” Walking into the Renaissance Revival building is akin to visiting a museum. On Dartmouth Street, two immense stone lions sculpted by Louis Saint-Gaudens stand guard by the main entrance. Inside, Bates Hall, the library's main reference reading room, is a 218-foot-long room with a barrel-arch ceiling soaring 50 feet high.

Visitors can take a free tour and learn all about the murals found throughout the library, including John Singer Sargent's series on the "Triumph of Religion." Other murals include works by French artist Pierre Puvis de Chavannes, who depicted eight library-centric disciplines in "The Muses of Inspiration," and Edwin Austin Abbey's "The Quest and Achievement of the Holy Grail."

John F. Kennedy Presidential Library and Museum John F. Kennedy Presidential Library and Museum

A must for any history buffs or fans of our nation's 35th president, this excellent library and museum details the life of President John F. Kennedy. Exhibits include his presidential papers; masses of Kennedy memorabilia, including re-creations of his desk in the Oval Office and of the television studio in which he debated Richard M. Nixon in the 1960 election; and artifacts from the U.S. space program. There's permanent display on the late Jacqueline Kennedy Onassis plus plenty of other artifacts and information about Kennedy's life and presidency. The building itself is quite striking and was designed by architect I. M. Pei.

Museumgoers say that while the museum is off the beaten path (it sits about 5 miles south of downtown on Columbia Point), it is well worth the trek thanks to the exhibits and staff. However, some wish the exhibits had a more detailed explanation of Kennedy and events during his life. The views from the museum are amazing, add some visitors.

Boston Harbor Islands National and State Park Boston Harbor Islands National and State Park

If you want to get outdoors in the greater Boston area, consider hopping a ferry (which operates from mid-May through mid-October) to the Boston Harbor Islands. This collection of 34 islands located in the Massachusetts Bay boasts plenty of things to do and see including historic sites, hiking trails, beaches, wildlife and much more. Popular islands include Spectacle, Georges and Peddocks, though ferries also go to Lovells, Grape, Bumpkin and Thompson.

The 114-acre Spectacle Island is a great option for those looking to hike. Here, you'll find 5 miles of trails, including one which leads to the harbor's highest hill, offering incredible views of Boston's skyline. If you’re looking for a place where you can sink your toes into the sand, head to Lovells Island. Here, you’ll find secluded shorelines as well as tide pools (when it's low tide, a whopping 71 acres are added to the island's land mass). Meanwhile, history lovers will enjoy a trip to Georges Island. Georges Island is home to Fort Warren, which the U.S. government used for patrolling and training Union troops as well as housing Confederate prisoners during Civil War times. Peddocks Island, one of the largest of the Boston Harbor Islands, offers a little bit of everything. This island is considered a prime camping spot and features scenic hiking trails that pass through coastal forests, headlands connected by tombolos and the biggest beach of any island. You'll also find a little bit of history thanks to Fort Andrews and a restored chapel from World War II.

Newbury Street Newbury Street free

Located in the Back Bay along eight blocks between Massachusetts Avenue and Arlington Street, Newbury Street is home to gorgeous 19th century brownstones. It's also Boston's premiere destination for dining and shopping. Newbury Street has been called one of the most expensive streets in the world, thanks in large part to the significant cluster of expensive shops on the lower end (by numbered address) nearest Arlington Street.

Starting at the higher end, by Massachusetts Avenue, you'll find more budget-friendly retailers like TJ Maxx and Forever 21, as well longtime local favorites Newbury Comics and Trident Booksellers. In fact, Newbury Comics' opening in 1978 was the catalyst that began the transformation of Newbury Street from a heavily upper-class retail destination to a hipper, trendier spot for everyone.

Samuel Adams Brewery Samuel Adams Brewery

Despite its location outside of city center, visiting the Samuel Adams Brewery is a popular stop for beer lovers. This brewery location acts as Samuel Adams' testing facility for new and specialty brews, which patrons can try. You can also take a guided tour of the facility to learn more about the brewing process.

Whether you're a local or a tourist, odds are you'll enjoy a visit to this brewery. Visitors say the staff is knowledgeable, but note there can be long entry lines.

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Cambridge Cambridge free

Cambridge, which sits about 3 miles northwest of Boston's city center, is home to both Harvard University and MIT , but there's more to see in Cambridge than just the schools themselves. The city features an impressive array of cultural institutions that feature collections and exhibitions ranging from fine art to technological innovations.

The Harvard Art Museums , which include the Fogg Museum, Busch-Reisinger Museum and Arthur M. Sackler Museum, house a wide range of periods, styles and mediums within its walls. Here, you’ll find a mix of modern photography, 13th century sculpture, paintings from legends like Georgia O’Keeffe, Picasso and Jackson Pollock, and much more. If you prefer history, head to the Peabody Museum of Archaeology & Ethnology , which boasts exhibits exploring everything from ancient Latin American cultures to the evolution of American eating habits and tableware to the lives of Native Americans. If science is more your speed, head to the Harvard Museum of Natural History to view dinosaur fossils, rare minerals and animal specimens from New England to Asia.

Beacon Hill Beacon Hill free

Beacon Hill is arguably Boston's most beautiful neighborhood. Located north of Boston Common , Beacon Hill is awash with quaint, cobblestone-lined alleyways, corners dotted with gas street lamps, stately townhouses affixed with bay view windows and vibrant, flower-filled window boxes. It's Beacon Hill's incredible style, a stunning mix of Federal and Greek revival architecture, that make this neighborhood an attraction in and of itself. And recent visitors couldn't agree more.

Travelers who venture to Beacon Hill are charmed by its beauty and say that it's the perfect place to take a long stroll and wander around. While here, make sure to make your way to noteworthy spots including the picturesque Louisburg Square and Acorn Street, the latter of which is one of the most photographed places in Boston. After, head down Charles Street, where you'll find restaurants, shops and bars. Fans of the TV show "Cheers" will want to walk down Beacon Street to find the bar that inspired the program.

Old North Church Old North Church

Most people who know anything about American history have heard of Paul Revere's famous midnight ride, when he rode through town to warn people about the arrival of British troops. Before heading off to Lexington, Revere gave orders at Old North Church. Robert Newman – the church's sexton – and Captain John Pulling Jr. – the church's vestryman – then climbed the steeple and held two lanterns as a signal that the British were indeed coming, but by sea.

The church itself, which is officially named Christ Church, is filled with beautiful relics from the past, including North America's oldest set of change ringing bells and chandeliers brought in from England in the early 1700s. The pews have a long history as well; Pew No. 54 was reserved for Paul Revere's son.

Boston Children's Museum Boston Children's Museum

With a giant milk bottle structure at the front of the building, it's hard to miss the Boston Children's Museum. Here, hands-on exhibits present a fun and engaging way for kids to learn about various sciences, culture, art and health and wellness, among other subjects. Among the museum's standout exhibits are "Construction Zone," where little ones can learn about and play with kid-sized construction equipment, "The Common," where kids play with color, games and music, and "Japanese House" – a 100-year-old authentic Japanese house reconstructed in Boston by Japanese carpenters.

Museumgoers praise the variety of engaging exhibits tailored to kids within different age groups and can't recommend it enough. Others warn the museum gets crowded, especially in the summer.

Rose Fitzgerald Kennedy Greenway Rose Fitzgerald Kennedy Greenway free

Boston is packed with cool outdoor spaces, but this nearly 1½-mile-long series of parks and gardens offers more than most. The Rose Fitzgerald Kennedy Greenway was established to link Boston's diverse neighborhoods through a series of lawns, parks and walkways that occupy a former highway tunnel. Since opening in 2008, visitors have flocked to this sprawling green space to enjoy temporary public art displays, bubbling fountains, numerous food vendors and a carousel. Plus, the park offers free weekly events, including food and art festivals, summer concert performances and seasonal fitness classes.

Many previous visitors said the Rose Fitzgerald Kennedy Greenway not only offers a much-needed respite from the city, but also an easy way to explore Boston with kids during the warmer months. And, in many sections of the Greenway, you're never more than a few steps away from the Freedom Trail .

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Boston Tea Party Ships & Museum Boston Tea Party Ships & Museum

This hands-on museum offers an entertaining look at one of Boston's pivotal moments. You can toss (fake) tea overboard, climb around replica ships and converse with period actors about Colonial issues. Exhibits at the museum, which is located on Griffin's Wharf (close to where the actual Tea Party occurred on Dec. 16, 1773) include 3D holograms, talking portraits and the Robinson Tea Chest, an authentic tea chest from the Boston Tea Party. Two of the three ships have been recreated, the Beaver and the Eleanor, which are fun to explore. The film "Let It Begin Here" depicts the events that immediately preceded the American Revolution. You can also grab a cup of tea or a snack in Abigail's Tea Room, which has one of the best views of the harbor around.

Visitors love the interactive nature of the museum and tossing tea overboard, saying their time there was entertaining for all ages. They also add that the guides are informative and stay in character.

Museum of Science Museum of Science

If you're traveling with young ones in tow, be sure to swing by the Museum of Science. Here, kids can learn about astronomy, earth sciences and anatomy, not to mention participate in some fun interactive exhibits. Budding scientists can examine the Arctic in "Arctic Adventure: Exploring with Technology" exhibit or play on swings to learn about physics in "Science in the Park." The museum also features the Charles Hayden Planetarium, where you can indulge your inner astronaut during shows. Meanwhile, at the Mugar Omni Theater, you'll feel like you're actually in the IMAX film thanks to its cutting-edge sound technology and five-story-high projection screen.

Although the museum is very kid-focused, past visitors said that young-at-heart adults and even teens will get a kick out of the museum's engaging displays and shows. Though most travelers spend about half a day exploring the museum, you could easily allocate an entire day to this attraction. Also, remember that separate tickets (which cost extra) are needed for some museum features, such as IMAX films, planetarium shows and the Garden Walk and Insect Zoo.

Boston Duck Tours Boston Duck Tours

Wander Boston for a couple of hours and you're sure to see a Duck Tour quacking its way through the streets (and waterways). These "Truck Duck" vehicles recreate the look of a DUKW truck used by the U.S. military during World War II and transport tourists all over the city by land and water. The tours drive past a number of landmark sites including the Old State House, Newbury Street , Prudential Tower, Public Garden and the Swan Boats, and Copley Square (home to the Boston Public Library ). Once launched into the water, you'll cruise down the Charles River checking out MIT, the Longfellow Bridge, as well as the Esplanade and the Hatch Shell. 

Besides giving tours around the city, Boston Duck Tour boats have been used in all of the victory parades since 2002 for the Patriots, Red Sox, Celtics and Bruins (the city's major teams for football, baseball, basketball and hockey, respectively). What started off simply as a way to roll the Patriots through downtown Boston for a Superbowl celebration has turned into a much-loved tradition that continues today.

Boston Symphony Orchestra Boston Symphony Orchestra

Even if you're not a classical music aficionado, you can't miss attending one of the Boston Symphony Orchestra's world-renowned performances at Symphony Hall. The BSO began performing in 1881. Today, the symphony performs everything from family shows to traditional concerts and Boston Pops – a lively performance filled with singing and a variety of music. The BSO performs at Symphony Hall from September through April, then heads to Tanglewood (which is about 130 miles west of Boston) in the summer.

Past spectators not only praised the world-class talent, but also noted the impressive acoustics of Symphony Hall as a main selling point for attending future concerts. If you can't score tickets to an orchestra performance, consider taking a free tour of Symphony Hall. Tours, which are offered in the fall, winter and spring, provide information about the property, as well as insight into the orchestra's musicians and conductors.

New England Holocaust Memorial New England Holocaust Memorial free

Gaze up at the six 54-foot glass towers that comprise the New England Holocaust Memorial, and you're bound to be awestruck. Dedicated in 1995, each haunting tower is etched with numbers. The 6 million numbers represent the Holocaust's victims, while the towers represent the six major death camps. There is also a granite path covered in quotes from survivors that leads visitors inside the towers.

Recent visitors described walking through the columns as an emotionally charged and unforgettable experience. The monument's location next to Faneuil Hall Marketplace makes it very accessible while walking the Freedom Trail .

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Paul Revere House Paul Revere House

For a glimpse of what life was like in the late 1700s, head to Paul Revere's former residence in the North End . The house, which is situated on the Freedom Trail , offers insight into how homes looked in Revere's time (it's even filled with period pieces, including fine silver). Inside, history fans can admire the building's sweeping beams, spacious fireplaces and some original furnishings owned by the Revere family.

If you like American history, travelers say you'll enjoy seeing the Paul Revere House. This house is small, though, so don't allot more than an hour to tour the property. Docents are friendly and knowledgeable.

Massachusetts State House Massachusetts State House free

The golden-domed Massachusetts State House is an important building for many reasons and is one of the stops on the Freedom Trail . The land it sits on was originally used as John Hancock’s cow pasture. It was designed by Charles Bulfinch and completed in 1798 and the cornerstone was laid by Samuel Adams in 1795. A copper dome was installed by Paul Revere in 1802 (later covered in gold). Nowadays, senators, state representatives and the governor conduct the Commonwealth's business here.

Free tours are offered by docents who explain the building's history and discuss the important art and architecture within. Make sure to look for the Sacred Cod in the House of Representatives Chamber. The almost 5-foot wooden cod symbolizes the importance of the salt cod industry to the area.

New England Aquarium New England Aquarium

Your kids will find plenty to love at the New England Aquarium, starting with the Atlantic harbor seals that hang out just beyond the ticket booth. Inside, you'll find thousands of marine critters to study, and at the center: the Giant Ocean Tank. This four-story tank includes a coral reef habitat that houses more than 1,000 underwater creatures including green sea turtles, eels and barracuda. In other parts of the aquarium, you'll find exhibits dedicated to penguins, sea jellies and seadragons, plus a six-story high projection movie screen with digital surround sound, where you can watch films about sea creatures and more. And don't forget to check out the Shark and Ray Touch Tank, which allows visitors to graze sharks and rays as they swim by.

While some visitors bemoan the aquarium's compact size (which, in turn, made for thick crowds), many appreciate the attraction's variety of animals. Several travelers also recommend watching a penguin or seal feeding.

USS Constitution USS Constitution free

U.S. News Insider Tip: Every July 4th, the USS Constitution takes her annual "turnaround" sail in Boston Harbor. The particular sail is the only one open to the public and the US Navy holds a lottery with the lucky winners getting to board "Old Ironsides." – Jill LeGrow

History lovers, boat enthusiasts and military aficionados alike can't miss the chance to board the USS Constitution. Docked at the Boston National Historical Park in Charlestown, this historic vessel is the world's oldest commissioned warship still operational today. It is helmed by United States Navy sailors, who also serve as the ship's guides. The ship's accompanying museums displays nearly 2,000 artifacts related to the ship's history.

Bunker Hill Monument Bunker Hill Monument free

Bunker Hill Monument is part of the Boston National Historical Park and a stop on the Freedom Trail . The first major battle of the American Revolution took place on Breed's Hill in June 1775, though originally it was supposed to take place on nearby Bunker Hill. Names aside, the British won the battle but fared worse than their American foes. The British sacrificed about nearly half of their 2,400 men; American casualties were between 300 and 500 out of an army of 1,400 to 1,800 soldiers. Construction of the monument started in 1827 and was completed in 1842. The 221-foot granite obelisk offers fabulous views from its observatory, though you have to work for it by climbing 294 steps to the top.

Start your visit at the Bunker Hill Museum, located across the street. Exhibits explain the Battle of Bunker Hill, the construction of the monument, and the history of Charlestown. Free tickets are required to climb the monument and you can also pick them up at the museum. Visitors enjoy the museum and say the monument is awe-inspiring and the grounds beautiful.

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View Boston View Boston

U.S. News Insider Tip: To save some cash on your sightseeing, pick up a Boston CityPass which allows you to visit up to four attractions (such as the Museum of Science , New England Aquarium , Boston Harbor City Cruise and View Boston) for one discounted price. – Jill LeGrow

Replacing the iconic Top of the Hub restaurant and Skywalk Observatory that closed in 2020, View Boston opened in June 2023 to offer 360 panoramic views of Boston from atop the 52nd floor of the Prudential Center. Taking over the top three floors of the Prudential Center, View Boston includes an observatory, a wraparound roof deck and indoor/outdoor cocktail bar called Stratus, and a floor with interactive exhibits such as a projection-mapped 3D model of Boston. There's also Beacon, a bistro offering seasonal beverages and food.

The Mapparium The Mapparium

Located at the Mary Baker Eddy Library, this three-story, stained glass globe never fails to elicit wonder. Designed by the architect of the Christian Science Publishing Society building, Chester Lindsay Churchill, the globe depicts the world as it was in 1935.

The "How Do You See the World" experience includes the globe; the "Our World: Mapping Progress," which highlights humanity's achievements since 1935; and "Points of Progress," where you can learn about significant events in human rights, scientific advances, exploration, and other fields. A 10-minute audio narration features clips from President Franklin D. Roosevelt, Jane Goodall, Wangari Maathai (a Kenyan Nobel laureate) and others. One of the coolest features of the globe is that it is a "whispering gallery." Stand at one end of the gallery while a friend stands at the other. Whisper something to them and they will be the only one to hear it.

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A Weekend in Boston Itinerary

It’s you’re planning to a spend a weekend in Boston, I’ve got your Boston Itinerary right here! These are all the restaurants you’ll want to check out, neighborhoods to visit, guided tours, and places to stroll!

This was such a last minute trip! 

My husband had been to Boston, Massachusetts before for a quick conference and came back raving about it. So when we needed a northern destination to check off of our bucket list on the way up to Canada, we flew into Boston Logan International airport for a weekend trip. I’ll be honest, this was a last minute trip so I got several of the recommendations on this list from my good friend and my sister. Both of them had been before and knew what I’d love to see and do!

I had always heard that the best times of the year to visit Boston was between September and November and luckily, the timing worked out perfectly for us. Cool morning and sunny afternoons, we clocked in about 15,000 steps a day and ate our weight in cannoli’s, pizza, and more!

A 2-3 day Boston Itinerary

Tourist attractions:.

• Newbury Street:  A shopping area lined with 19th century brownstones. They have tons of high end stores and boutiques. Even if you aren’t planning on buying anything it’s great to walk around and take in the sights!
• Boston Public Library:  This is a beautiful work out art! For as long as I can remember, I’ve always wanted to visit Bates Hall with its iconic green lamp room! Then walk across Boston’s Copley Square to the Trinity Church.
• Acorn Street:  This is one of the most photographed streets in the city! This row of houses is considered highly prestigious and there are signs everywhere that say it’s a private lane. Visitors are asked to respect it and stay off of the street. But you can always stand at the corner and check it out!
• Charles River Esplanade:  Gives you  a beautiful view of the Boston skyline!
• Beacon Hill:  A great neighborhood to check out on the way to or from Acorn Street. The old corner bookstore (Beacon Hill Book Store) is beautiful and you could spend hours getting lost in there!
• Boston Commons:  You can start walking the Freedom Trail here. The Freedom Trail start in the Boston Common, to the Old North Church in the North End and the Bunker Hill Monument in Charlestown. This is rich in America’s history.
• Boston Public Garden:  Make way for Ducklings are located here and they are the cutest! You should also check out the Lagoon Bridge.
• Harvard University:  Absolutely stunning college campus located in Cambridge, MA. We weren’t really planning on adding this to our itinerary and since we skipped the Freedom Trails (a dream for a history buff, but we just aren’t) we decided to use the afternoon to Uber into Cambridge. Afterwards, head to the amazing Uyghur restaurant in the food reccs!
• Quincy Market:  Historic market located right across from Faneuil Hall Marketplace in Downtown Boston. These are both great place to check out and grab a few souvenirs, clam chowder, and for crowd watching.
• Isabella Stewart Gardner Museum: tickets are $20 for general admission and they do offer a beautiful afternoon tea service at the cafe for an extra cost. Though it is a bit pricey, so definitely budge for this if it’s something you’d enjoy!
• Catch a Red Sox game:  if you’re a baseball fan, this is not to be missed. The Boston Red Sox play at Fenway Park during the season.

Recommended Tours:

• Boston Ghosts and Gravestones Trolley Tour:  This boards off of 200 Atlantic Ave, right in front of the Marriott. This is steps from the Boston harbor. We had dinner at Regina’s Pizza, grabbed Mike’s then walked over for the tour. Keep in mind that though it is a trolley tour, there are several times you have to hop off and walk (sometimes up hill) to historic landmarks such as the Granary Burying Ground and King’s Chapel Burying Ground. We had a few people on the tour that hopped off and didn’t come back, because of mobility issues. The tour guide carries a little lantern as you walk to burying grounds and honestly, for an all-things-spooky fanatic, this was one of my favorite things to do in Boston! Buy tickets here .
• Boston Duck Tours:  This is a great way to see the city if you are short on time on a guided tour without having to leave the duck mobile! The tour guides take your through sites such as the Theater District, Massachusetts State House, Fenway Stadium, and many others before giving you a water tour! We started the tour from New England Aquarium and returned there before walking around the harbor front for a bit.

Where to Eat in Boston:

• Located at 11½ Tatcher St. Boston, MA
• Mike’s Pastry:  I have an un popular opinion! I didn’t care for Mike’s Pastry. There was so much hype surrounding this dessert shop and honestly, it was kind of meh. Overly sweet, not much flavor to the desserts. But you should still try it for yourself!  A quick heads up, they only accept cash!
• Modern Pastry:  We didn’t get a chance to try this shop, but I wouldn’t be doing my Boston itinerary justice if I didn’t mention it. Many people try both this and Mike’s and like to pick their favorite!
• Ogawa Coffee:  They had the most amazing drip coffee. And my thing is, if you can do drip right, it’s worth checking out!
• Bruegger’s Bagels:  For a quick, grab and go breakfast!
• Located at 105 Huntington Ave. Boston MA 20199.
• Located at 300 Northern Ave, Boston, MA 02210.
• Located at 645 Cambridge St, Cambridge, MA 02141
• Located at 70 Charles Street Boston, MA 02114 (this is the Beacon Hill location but there are others in Back Bay, South Boston, Fenway, and several others)

FAQs about Boston:

I’d say 2-4 days depending on how quickly you can get through attractions and how much of a history buff you are! If you are into history, give yourself plenty of time as there is plenty to see in Boston!

Yes, and you should! Boston is not a city where you want to drive! Instead opt to clock in plenty of steps and use Uber for when your feet just can’t handle another step. The key is to center yourself in the city based on the places you’d like to visit so that you are walking and not Ubering everywhere.

I would say that Boston has something to offer for everyone and is definitely worth adding to your itinerary. With that said, would I fly from Houston to Boston just to see Boston? No. But I would definitely recommend it as a city to hit on your east coast tour!

Layers! Depending on the time of year you visit, Boston can start off cool and warm up throughout the day before it dips again in the evening. Layering is the best way to stay comfortable.

Of course, these are just some of the many things to do in Boston, so if I missed your favorite, feel free to leave it in the comments below 🙂

If you like this, you might also like:

• Fall Things to do in Woodstock, VT
• Experiencing Fall in Stowe, Vermont
• Girls Trip to New York
• 19 Tips for Visiting the Wizarding World
• A Weekend in Chicago

published on Oct 19, 2023

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17 Fun Weekend Getaways from Boston

Boston is truly one of the best cities in the United States –and that’s even before you consider just how many incredible weekend getaways from Boston there are!

As the largest city in historic New England, Boston is filled with some of the most amazing restaurants and photo spots east of the Mississippi River.

However, everyone needs a getaway sometimes, and no matter what your travel style, there are enough short trips from Boston to add to your bucket list, that you can stay busy in the northeast for years!

Some places on this list can be visited utilizing public transportation, such as the Peter Pan bus, Greyhound bus, or Amtrak.

For the most part, though, you will need to either have your own car or rent a car for these weekend trips from Boston.

Here are the best weekend getaways from Boston–plus some tips on how to plan your trip!

Note : This blog post was written for Our Escape Clause by former Boston resident Krystianna of Volumes & Voyages . Thanks for joining us, Krystianna!

Table of Contents

Boston Weekend Getaway Travel Tips

The best cities for weekend getaways from boston, best small-town weekend trips from boston, nature-focused boston weekend getaways.

Some links in this post may be affiliate links. If you make a purchase through one of these links, we may earn a small commission at no extra cost to you. Please see our disclosure policy for more detail.

Before hitting the open road, here are some tips to keep in mind when planning a short getaway from Boston!

Pack for all types of weather.

New England is notorious for having strange and unpredictable weather.

Sometimes, there is a random snow day in May, and sometimes it will randomly be really warm in the middle of November.

For the most part, you’ll want to pack for the season, but don’t be afraid to also pack layers because you genuinely don’t know what you’re going to get !

Be prepared to make stops along the way!

There are so many great places to visit in the northeast, and you will most likely pass by some of these spots along your drive.

Try to plan on pulling off at least a few times during your ride to or from your destination if you’re driving a car.

Especially if you’re heading up to Vermont or Maine, you’re going to pass by some epic viewpoints driving from Boston.

Rental car prices can vary dramatically depending on pickup location.

Don’t just rent from the first rental car place that you find.

Instead, be sure to check out other rental car options in the area , including Boston’s suburbs.

You might be surprised at the deals you’ll be able to find by heading outside the historic center!

For browsing, we recommend shopping with Discover Cars !

They’ll compare prices and inclusions from multiple brands to ensure you’re getting the best deal for your trip.

Compare rental car prices and inclusions with Discover Cars today!

Portland, Maine

Nestled on the coast of southern Maine, Portland is one of the easiest weekend getaways from Boston and is a classic New England getaway.

While you’re there, be sure to stroll around the Old Port, admire Portland from above at the Portland Observatory, snap photos at the Portland Bug Light, tour the beautiful Victoria Mansion, and visit a few of Portland’s famous breweries.

And, of course, you can’t visit Portland without heading out to John Williams Park and admiring the famous Portland Head Light for yourself!

Distance from Boston

1 hour, 45 minutes by car or 2 hours, 30 minutes by train.

How to Get to Portland from Boston

While driving is the easiest way to visit Portland (you’ll have more options for exploring and day trips while you’re there), there are also direct trains between Portland and Boston, making this one of the best Boston weekend trips for travelers who don’t want to drive.

Where to Stay in Portland

• The Francis: This hotel is a historic landmark in the Bramhall neighborhood, near the Art District, and has a fabulous on-site spa. Perfect for a weekend relaxing.
• Best Bower: Simple, clean, and classic with all the cozy luxuries you could wish for from your weekend trip.

New York, New York

New York City is America’s most popular city for a good reason: it’s loaded with great things to do!

Absolute must-sees during a weekend in New York City include Central Park, the Statue of Liberty, Times Square, and the Empire State Building.

Fans of museums and history should also opt to visit the Metropolitan Museum of Art or the Modern Museum of Art.

If you’re lucky enough to be visiting during the wintertime, you absolutely must head to Rockefeller Center to see the giant Christmas tree!

The Rockettes also perform in the winter months. More local attractions like Brooklyn’s Dyker Heights Christmas lights are also worth going out of your way for!

There are lots of great neighborhoods to stay in during your weekend.

Just remember that New York City is vast, and the closer to the city center you are, the less you’ll have to spend on transportation, and New York City traffic can be horrendous .

Opt to try to stay near SoHo for its charming architecture, Greenwich Village to be in the trendy part of the city, or Brooklyn, which is known for being hipster and upbeat.

How to Get to NYC from Boston

The easiest way to get to New York City is to drive, but having a car in NYC can be a hassle!

We recommend taking the Amtrak or the Megabus from Boston’s South Station–the train is a bit more comfortable, and less likely to experience delays due to traffic (a big risk with bus travel between the two cities) but also much more expensive than taking the bus!

Where to Stay in New York City

• Omni Berkshire Place: Just 805 meters from Central Park this Manhattan hotel is a great choice for your weekend trip. Soak in the huge bathtubs and wake up to views of the NYC skyline.
• Sixty Soho: In the heart of the stylish Soho district this is a great spot for your trip. Sip cocktails on the rooftop bar and have your own New York minute.

Burlington, Vermont

Burlington is drastically different from Boston, but that’s what makes it the perfect weekend getaway spot.

This quaint, lakeside city in Vermont is the most populated part of the whole state.

However, it only has a population of 43,000 people, with the majority of citizens being college students at Champlain College and the University of Vermont.

One of the best things to do in Burlington is to go to Church Street, which is a marketplace quite like Newbury Street and Quincy Market in Boston.

It’s a beautiful cobblestone street lined with areas to shop.

Other popular spots include the Ethan Allen Homestead Museum, Waterfront Park, and the Fleming Museum of Art.

The Ben & Jerry’s Factory is only a short ride away from Burlington, so plan on taking a detour there on your way to Burlington or on your way back to Boston.

There are free tours here offered daily, and you honestly won’t want to miss it.

3 hours, 15 minutes.

How to Get to Burlington from Boston

It’s most simple to drive to Burlington using I-93 N and I-89 N.

It is possible to take an Amtrak if you have the time, but you have to make a significant detour to New York City since there isn’t a direct route to Burlington, which can take almost a day.

Where to Stay in Burlington, Vermont

• Green Mountain Suites: The perfect spot for a classic cozy Vermont trip with open fireplaces, fluffy blankets, and an onsite hot tub.
• Blind Tiger: Another gorgeous luxury option is this hotel with a stunning private garden and comfortable rooms.

Newport, Rhode Island

Just south of Boston is the gorgeous city of Newport, Rhode Island , one of the most romantic places in the USA , and a fun getaway from Boston!

It’s most famous for its large mansions that are home to many of America’s celebrities, and in many cases, date back to the Gilded Age.

One of the best activities to do here is to go on a trolley tour, which will bring you around to many of the area’s best mansions.

Other fun things to do in Newport include swimming and shopping.

There’s also the Newport Art Museum, Castle Hill Lighthouse, the Redwood Library and Athenaeum, and Brenton Point State Park.

This area is unlike many of New England’s other cities because it really doesn’t feel like a city at all!

1 hour, 20 minutes.

How to Get to Newport from Boston

It’s easiest to travel to Newport by car, but you could also hop on two buses (one from Boston to Providence and then Providence to Newport) in under 2 hours.

Where to Stay in Newport

• Ivy Lodge: Stay in a classic mansion house complete with a turret and gothic woodwork. In the heart of Newport Mansion District and less than a mile from Newport Harbor, all rooms also have fireplaces for the ultimate romantic weekend evenings.
• America’s Cup Inn: Set along a cobblestone street with gaslights, and decorated with colonial period furnishings, this is a classic New England B&B. Rooms have 4-poster mahogany beds or antique wicker furnishings.

Mystic, Connecticut

Mystic, Connecticut, is a quintessential New England town.

It’s located right on the water and is breathtaking–there are great views almost everywhere you look !

Fun places to explore include the Seaport Museum, Misquamicut State Beach, Ocean Beach Park, and the Napatree Point Conservation Area.

Honestly, if you’re looking for a small town right on the coast, then Mystic is the place for you!

1 hour, 40 minutes.

How to Get to Mystic from Boston

Driving is the simplest way to get straight to Mystic, but you could also take the Amtrak straight from South Station in Boston.

This will only take 1.5 hours!

Where to Stay in Mystic

• The Whaler’s Inn: The Mystic River Bascule is around the corner from this historic hotel in Mystic. Wake up with designer bed sheets and mattresses and enjoy an amazing breakfast before exploring Mystic.
• House of 1833: Step back in time with this charming B&B in Mystic. Packed with historical details, antiques, and quirky collectibles, this is a great choice for a weekend in Mystic.

Bennington, Vermont

The small town of Bennington, Vermont is located in the southwest corner of the small state, not far from either Vermont’s border with New York or Massachusetts.

It serves as the perfect weekend getaway because it’s so vastly different from Boston!

While there, be sure to check out some local restaurants, including Blue Benn Diner, Jensen’s, and Papa Pete’s.

There’s also a lovely brewpub called The Tap House, which is fantastic.

If you’re a fan of the outdoors, be sure to do one of the many hikes in the area, like the hike to the White Rocks.

2 hours, 50 minutes.

How to Get to Bennington from Boston

It’s easiest to drive here from Boston. It’s possible to take multiple buses, but this can turn into a whole day ordeal.

Where to Stay in Bennington

• South Shire: This lovely hotel offers a homestay environment with added hotel touches such as a hot tub and a fabulous breakfast each morning.
• Four Chimneys Inn: Housed in a mansion on an 11-acre estate with an extensive garden, this stunning property is perfect for your weekend getaway. With four-poster beds and classic furnishings throughout you will feel truly spoiled.

Manchester, Vermont

Manchester is located only 30 minutes north of Bennington, Vermont, but if possible, it is even more charming!

This town is historic and is filled with some of the most beautiful buildings in all of Vermont, and is also a popular place to go shopping.

Be sure to check out the Manchester luxury outlet shops and also the Northshire Bookstore.

Similar to Bennington, there are a few hikes in the area that are worth doing, and these ones are a lot less strenuous than other hikes in southern Vermont. 

How to Get to Manchester from Boston

Driving is the only realistic way to get to Manchester from Boston.

Where to Stay in Manchester

• Kimpton Taconic Hotel: This mountain view hotel is a great weekend choice in Manchester. Take a leisurely soak in the huge bathtubs, relax by the pool or just enjoy the comfortable surroundings.
• Reluctant Panther Inn: This quirky named Inn also has an excellent onsite restaurant, as well as spacious rooms, beautiful wood furnishings, and fireplaces.

Saratoga Springs, New York

Saratoga is a quaint town in New York that is most famous for hosting the Saratoga Races!

These occur every summer, so if you’re lucky enough to be visiting during the summer months, then you’ll want to try to go and spend at least one day at the horse races.

It’s truly an unforgettable experience.

Other popular places in Saratoga to explore include Saratoga Spa State Park, Saratoga National Historical Park, and the National Museum of Dance & Hall of Fame.

There’s also a really gorgeous shopping area in downtown Saratoga, which is home to the Northshire Bookstore’s New York branch.

This bookstore is beautiful and it’s great to support local sellers.

How to Get to Saratoga from Boston

You’ll want to drive to Saratoga from Boston. You could also utilize the bus, but it will take a lot longer.

Where to Stay in Saratoga

• Batcheller Mansion Inn: As one of America’s great Victorian houses, built in 1873 and the site of many historical moments in Saratoga history, this is a stunning place to step back in time for your weekend trip. Beautifully preserved and steeped in history, well worth the trip!
• Saratoga Casino Hotel: For a more resort-style weekend trip this hotel is a perfect choice. Rooms are peaceful and huge, and there is a free shuttle service to take you into town to explore.

Portsmouth, New Hampshire

For a classic, small-town New England getaway complete with historic homes, a beautiful harbor, plenty of seafood restaurants, and a relaxed vibe, you can’t beat exploring the best things to do in Portsmouth, New Hampshire !

This gorgeous New Hampshire Seacoast is a New Englander favorite for good reason.

While you’re there, visit the popular Strawbery Banke Museum, shop the charming boutiques, explore downtown and the harbor on foot, and enjoy a seafood dinner on the water.

1 hour, 15 minutes.

How to Get to Portsmouth from Boston

You can reach Portsmouth from Boston by either bus or car.

Where to Stay in Portsmouth

• Ale House Inn: Located in a historic building that once housed a brewery, and with a complimentary bike hire this is a great choice for your weekend in Portsmouth.
• The Hotel Portsmouth: Located in Downtown Portsmouth this charming Victorian manor house has spacious rooms and is a short walk to all the amenities.

Acadia National Park, Maine

The first national park east of the Mississippi is absolutely one of the best weekend trips from Boston for those looking for some hikes, some stunning coastal views, and some of the best sunrises and sunsets in New England!

Some of the best things to do in Acadia National Park include watching the sunrise on Cadillac Mountain (during part of the year, this is the first place the sun rises on the continental USA!), strolling around Jordan Pond, hiking the Beehive Trail, checking out the Bass Harbor Headlight, and exploring the Carriage Roads.

Don’t forget to enjoy the charming things to do in Bar Harbor while you’re there, which is home to great restaurants, a cozy New England vibe, and plenty of beautiful places to stay!

4 hours, 30 minutes.

How to Get to Acadia NP from Boston

The best way to reach Acadia National Park from Boston is to drive. 

While there is a shuttle bus at the park in the summer, it’s vastly easier to visit Acadia with a vehicle.

Where to Stay in Acadia National Park

• Acadia Inn: Within 1 mile of the park and with its own nature trail that extends into the park this is the perfect spot to base yourself in Bay Harbor near the park.
• Bar Harbor Grand Hotel: Another great option in Bay Harbor is this palatial manor hotel with a swimming pool and hot tub.

North Adams/Berkshires, Massachusetts

The Berkshires is a beautiful region of western Massachusetts that is always highly overlooked and underrated.

This area is very rural land and is filled with lots of great outdoor activities.

This is also the perfect place to go if you are interested in seeing fall foliage near Boston that is (maybe) slightly less crowded than the White Mountains of New Hampshire.

North Adams serves as the perfect home base for exploring the Berkshires.

In North Adams, be sure to check out the Natural Bridge State Park, Windsor Lake, and Cascade Trail.

If it ends up raining a bit while you’re there, don’t worry, there are also lovely art museums and history museums worth exploring.

2 hours, 40 minutes

How to Get to North Adams from Boston

You can only get to North Adams from Boston by car, but you’ll pass some magnificent scenery along the way!

Where to Stay in North Adams

• Tourists: This incredible hotel is the perfect place to stay for your weekend trip. Designed like something out of an architecture magazine but still comfortable, warm, and welcoming.
• The Lodge: Another fabulous option set as private cabins with stunning decks to sit and enjoy the sunset.

Lake Champlain, Vermont

Lake Champlain is a gorgeous lake in Northern Vermont and Northeastern New York.

It’s absolutely beautiful and is filled with lots of great outdoor activities, like biking trails, hiking trails, kayaking, canoeing, swimming, and more.

The lake covers a lot of ground, so there are many great towns to set yourself in for exploring the area.

Of course, you could opt to stay in Burlington, but other popular areas to stay include St. Albans and Shelburne.

You could also choose to stay on the New York side, such as in Plattsburgh or Champlain.

Just know that the prices can drastically change depending on where you opt to stay !

4 hours, 35 minutes.

How to Get to Lake Champlain from Boston

Like most of the outdoorsy places, you do have to drive to get to Lake Champlain from Boston.

Where to Stay in Lake Champlain

• Green Mountain Suites: The perfect spot in Burlington for a classic cozy trip with open fireplaces, fluffy blankets, and an onsite hot tub.
• Back Inn Time: This aptly named hotel is perfect for a stay in St. Albans . Surrounded by pretty flower gardens, four covered porches, and two decks, relax in these comfortable surroundings during your weekend trip.

Kennebunkport, Maine

Kennebunkport is a beautiful town and coastal area in southern Maine.

The scenery here is absolutely breathtaking, from the Goat Island Lighthouse to Ocean Avenue.

Some popular places to explore here include Gooch’s Beach, Walkers Point, and the Rachel Carson National Wildlife Refuge.

There are lots of more secluded areas around Kennebunkport that you could easily stay in.

This makes it perfect for a quiet escape from the city, and ranks it among the best weekend getaways from Boston!

1 hour, 30 minutes.

How to Get to Kennebunkport from Boston

The only way to get to Kennebunkport from Boston is to drive, but you’ll drive right along the coast the entire time!

Where to Stay in Kennebunkport

• AWOL Kennebunkport: With cabin and suite options this is a perfect zen getaway in Kennebunkport. Enjoy the garden or the sun terrace between exploring the surrounding area.
• Waldo Emerson Inn: This classic New England inn is a great choice for your weekend trip. Relax by the fire or take advantage of the free bikes to explore the area.

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About Kate Storm

In May 2016, I left my suburban life in the USA and became a full-time traveler. Since then, I have visited 50+ countries on 5 continents and lived in Portugal, developing a special love of traveling in Europe (especially Italy) along the way. Today, along with my husband Jeremy and dog Ranger, I’m working toward my eventual goal of splitting my life between Europe and the USA.

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The Best Weekend Getaways from Boston

Don’t believe anyone who tells you to skip New England just because of its famously raw winters —this time of year, the landscape is as alive as ever with natural beauty, any crowds that accumulated over the summer and fall have thinned, and getting away feels even more apropos. With COVID-19 protocols allowing for safe, responsible travel within the region and between most of the New England states, it’s as easy as ever to appreciate having so much at your fingertips in this corner of the country. Here, we’ve hand-picked some of our favorite winter retreats from Boston —whether you’re looking for an alpine adventure, a bracing walk along the ocean, or just some R&R in the countryside.

All listings featured on Condé Nast Traveler are independently selected by our editors. If you book something through our links, we may earn an affiliate commission.

Omni Mount Washington Resort (Bretton Woods, NH).

Omni Mount Washington Resort—Bretton Woods, New Hampshire

The alpha and the omega of New England’s historic grand hotels has continued to get even grander after 2020 renovations to its iconic 0ld World-style dining rooms, and the brand-new expansion of its Presidential Wing (set to open any day now). The hotel sits on a once-in-a-lifetime piece of real estate overlooking the spectacular White Mountains, just across the street from Bretton Woods Mountain Resort, the state’s largest ski resort. 

Book now: From $249 per night, expedia.com

Spruce Peak (Stowe, VT)

The Lodge at Spruce Peak—Stowe, Vermont  

This posh ski-in, ski-out escape takes the schlep out of winter sports, thanks to its central location at Stowe Mountain Resort—it’s entirely possible to valet your car at check-in and not need to see it again until you leave. Make sure to book a spa appointment, where treatments such as the CBD and cryotherapy massages are a godsend for tired ski legs. The best part? It’s located stumbling distance to the Whistlepig Pavilion, one of Vermont’s most coveted spots for après-ski, now open with private drinking and dining pergolas. Unclick your ski boots, order some raclette and a Barrel-Aged Old Fashioned made from WhistlePig’s award-winning 10 Year Straight Rye, and it’s hard to imagine a better après-ski on this side of the Alps , or anywhere.

Book now: From $359 per night, skylark.com

Tourists Hotel (North Adams, MA).

Tourists Hotel—North Adams, Massachusetts

In an area known for old-school B&B’s and sprawling country estates, Tourists embodies a new wave of energy coursing through the Berkshires. The spare design is decidedly hip, and there’s even an on-staff “art and adventure coordinator” to help you unlock the best this region has to offer. The location, after all, is perfect. Within spitting distance you’ll find not only cross-country ski trails and winter hiking paths (including the Appalachian Trail ), but the hotel is a short drive away from world-class art museums at Mass MoCA and the Clark Institute , the latter of which just installed Ground/work, an enormous site-specific outdoor sculpture walk.  

Book now: From $339 per night, touristswelcome.com

Field Guide (Stowe, VT).

Field Guide Lodge—Stowe, Vermont

Ski bums will appreciate the competitive pricing at this intimate Green Mountain outpost —as well as the free shuttle to nearby Stowe Mountain. Part midcentury mod, part Scandinavian hygge, and part Vermont cabin , this boutique hotel has just 30 rooms, so it feels a lot more intimate than some of Vermont’s more imposing, impersonal ski resorts. That intimacy is on display the second you enter the guest lobby, where a crackling communal fireplace and stacks of board games await after a long day of exploring the outdoors.

Book now: From $139 per night, expedia.com

Wheatleigh (Lenox, MA).

Wheatleigh—Lenox, Massachusetts

Despite the sweeping Berkshires hillsides and quintessentially New England forests that surround the hotel, stepping into the lobby of this stately retreat feels more akin to arriving at a grand Italian palazzo or French country chateau. Before it was a hotel, it was a 19th century country home for Manhattan real estate tycoon Henry Cook, and even today feels less like a hotel and more like a glamorous private estate. No two rooms are alike, and the precisely manicured grounds seem to roll on forever into the distance. The area is even more tranquil and serene come winter. 

Book now: From $655 per night, skylark.com

Inn at Hastings Park (Lexington, MA).

Inn at Hastings Park—Lexington, Massachusetts

Driving for hours on icy winter roads not quite your thing? Consider this intimate, historic inn located in historic Lexington—which can be reached from Back Bay in about twenty-five minutes flat. Each of the 22 guest rooms has its own design and color palette, with locally inflected design accents like artisan wallpapers and hand-woven blankets. New for this winter are outdoor dining igloos, where you can take in a socially distant private dining experience under the stars. It’s close enough to Boston to do as just a single overnight getaway, but far enough that it still feels special. Trust us, the Berkshire Pork Chop with bourbon apple braised kale at the Inn’s award-winning Town Meeting Bistro is reason enough to make the drive out.

Book now: From $245 per night, expedia.com

Blue Hill Inn (Blue Hill, ME).

Blue Hill Inn—Blue Hill, Maine

Most of Maine’s beautiful coastal resort towns shut down for the winter, but luckily that’s not the case on the Blue Hill Peninsula just south of Mount Desert Island . The locals-endorsed Blue Hill Inn keeps its 11 guest rooms going all year long. In fact, it seems that the action only seems to ramp up during the colder months—cross-country skiing, ice fishing, cooking classes, craft fairs, sleigh rides, and good old-fashioned winter beach walks are all on offer. Of course, just enjoying your room and curling up by your very own wood-burning fireplace is an option, too.

Book now: From $150 per night, bluehillinn.com

Kimpton Taconic (Manchester, VT).

Kimpton Taconic—Manchester, Vermont

The Kimpton Taconic is a ski hotel where you can also bring non-skiers. Yes, there are three fantastic ski resorts within a one-hour drive, but for those less inclined toward winter sports, the Taconic’s location in Manchester still offers plenty of art galleries, historic sites, restaurants, and shopping, much of which is within walking distance. No matter which adventure you choose, make sure to finish your day at the Taconic’s fantastic restaurant Copper Grouse, where local ingredients like Vermont beef and artisanal cheeses make for a tempting—and very satisfying—menu.

Book now: From $159 per night, expedia.com

Ocean House (Westerly, RI).

Ocean House—Westerly, Rhode Island

At this Relais & Chateaux property , the only thing that competes with its fine dining and exceptional service is the panoramic ocean view—most rooms have at least a partial view of the water. When you aren’t busy going for a moody Folklore -ish winter walk on the premises’ private beach (where you might just bump into the hotel’s neighbor Taylor Swift), indulge in a treatment at the 12,000-square-foot OH! Spa.

Book now: From $530 per night, skylark.com

Castle Hill Inn (Newport, RI)

Castle Hill Inn—Newport, Rhode Island

Ever been to Newport in the off-season? Consider it much the same as the Hamptons in the winter—sure, maybe a few of the restaurants are closed, but the drop-off in crowds makes it that much easier to experience the beauty of the landscape. As one of Newport’s most desirable hotels during the warmer months, Castle Hill Inn , which dates back to 1875, makes a serious case for winter visits, too. This year, the Inn will forgo its traditional January closure, offering dining and accommodations every weekend all winter long—when the room rates go for half to one-third of what they cost during peak summer. Splurge for one of the dreamy Beach Houses, which feature gas jet fireplaces, plush King beds, and elegant French doors opening up onto panoramic Atlantic Ocean views.

Book now: From $330 per night, expedia.com

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36 Hours in Boston

By Jenna Russell July 4, 2024

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By Jenna Russell Photographs by Simon Simard

Jenna Russell is the New England bureau chief for The New York Times and previously reported for The Boston Globe.

In Boston — oft-beset by slush and cynicism — summer brings a deep sigh of relief, as hunched shoulders finally relax and beer gardens pop open like tulips. First-term mayor Michelle Wu, 39, the first woman and person of color elected to lead the city, has brought an ambitious environmental agenda and new ways of looking at the urban landscape . The result is a destination steeped in history, as ever, with reinvented outdoor spaces for drinking, dining and recreating, and more change in the air. Waterfront redevelopment has spread farther and wider, spawning new harbor-adjacent art spaces and breweries, while a forward-looking focus on water transportation means more ferries and water taxis to get you where you’re going, while enjoying sparkling views and salty breezes.

Recommendations

• Fenway Park , the home of the Boston Red Sox and the oldest, smallest ballpark in baseball, offers daily tours full of colorful history.
• Yvonne’s serves elegant food and unusual cocktails, with ingredients that include marshmallow, carrot and salted sage, in a dazzling reinvented space.
• The Boston Harborwalk , a “linear park” stretching more than 40 miles, traces the zigs and zags of Boston’s waterfront.
• The ICA Watershed , a seasonal satellite of Boston’s Institute of Contemporary Art, brings free exhibitions to harborside East Boston every summer.
• UnCommon Stage , an outdoor performance space run by Emerson College in partnership with the city, hosts free performances in a beer garden on Boston Common , the country’s oldest public park.
• “ The Embrace ,” a new public sculpture on the Common, celebrates the love between Dr. Martin Luther King Jr. and Coretta Scott King, who first met as students in Boston.
• The Granary Burying Ground , established in 1660, is the final resting place of the founding fathers Samuel Adams, John Hancock and Paul Revere (plus Benjamin Franklin’s parents).
• The African Meeting House on Beacon Hill, part of the Museum of African American History , is considered the oldest surviving Black church building in the country.
• The John F. Kennedy Presidential Library and Museum explores political history and the mystique of the Kennedy family in an architectural gem on Dorchester Bay.
• Bakey is a bakery with Danish-Israeli roots, across the street from Boston Common.
• Temple Records pays tribute to Japanese listening bars and serves sushi downstairs.
• Time Out Market Boston , a massive food hall near Fenway Park, showcases a range of Boston favorites like lobster rolls and three-way roast beef sandwiches.
• Carmella’s Market is an old-school Italian market in East Boston for giant takeout subs.
• Downeast Cider House offers four-flavor flights of cider in its tap room near the waterfront.
• Tea by the Sea is a spacious harborside cafe offering bubble tea and smoothies.
• The Tall Ship is a floating oyster bar with sunset views in East Boston.
• Rincon Limeno , a neighborhood favorite, has a friendly vibe and authentic Peruvian food.
• Sullivan’s is a summer institution for hot dogs, lobster rolls and ice cream in South Boston.
• Dorchester Brewing has a rooftop deck and tasty smoked meats from M&M BBQ .
• Comfort Kitchen in the Dorchester neighborhood has won accolades for its global comfort food, including okra, plantains, jerk-roasted duck and curried monkfish.
• Music Research Library is a light-filled record store on a quiet street, with a peaceful, library-like ambience and two listening stations.
• Beacon Hill Books & Cafe opened in 2022 but feels like a neighborhood institution, with five floors of books in a charming 19th-century townhouse.
• December Thieves is a Beacon Hill boutique known for unusual jewelry, like rings of polished resin and dangling silver earrings shaped like bare winter branches.
• Yacht Haven Inn & Marina , on Commercial Wharf in the historic North End, has an unrivaled harborside location. The boutique hotel has 10 spacious rooms, some with private decks overlooking the water; you can also rent a slip to berth your boat. Rooms start at around $500.
• The Verb Hotel , next door to Fenway Park, has won a faithful following for its funky take on hospitality, with turntables in every room and a lending library of 1,700 records in the lobby. Breakfast (included) is way above average, with live music and fruit smoothies made to order; the former Howard Johnson’s even has a heated outdoor pool. Rooms start at around $300.
• citizenM , a no-frills budget option, offers a prime Boston location close to historic attractions and the Italian restaurants of the North End, and next door to the TD Garden, home of the Boston Celtics and the Boston Bruins. Rooms start at around $200.
• Boston is compact and largely walkable , though you’ll need other transport to reach some of its most dynamic neighborhoods. Its beleaguered subway system, known as the T , has struggled with delays and breakdowns of late, but remains the cheapest, fastest way to get around in many cases. A CharlieCard can be purchased at any station, and widespread testing of one-tap credit card entry is under way. The Massachusetts Bay Transit Authority, known as the M.B.T.A., also offers a beefed-up summer ferry schedule (Charlestown and East Boston routes $2 to $4 one way).

UnCommon Stage

Kick off the weekend in the oldest city park in the United States, the Boston Common , where a new summer performance space run by Emerson College, UnCommon Stage , features free live music in a beer garden pouring classic drafts from the Boston mainstay Harpoon Brewery . When you’re ready for a stretch, amble over to “The Embrace” and debate the merits of the Common’s newest and most hotly debated public monument , a massive, semi-abstract bronze work paying tribute to the love between Dr. Martin Luther King Jr. and Coretta Scott King, in the city where they met. Then drop in across the street at Bakey, a fragrant pastry showcase with Danish-Israeli roots, to stock up on chocolate, almond or raspberry babka ($6) for the morning (or a late-night snack).

Downtown Crossing

In the city’s Downtown Crossing shopping district, Temple Place has become a lively restaurant row of late, dense with clever concepts like the Wig Shop , a cocktail lounge tucked behind a storefront that remains a dead ringer for the wig shop it once was. Steps away, the new Temple Records is a tribute to the “listening bars” of 1950s Japan, with a custom sound system and an eclectic collection of vintage vinyl. Sip a pale green Off Minor cocktail (gin, Midori, basil, yuzu, absinthe, $16) and snack on addictive karaage fried chicken ($16) while trying to identify the album in rotation. Hidden one floor below, Sushi@Temple Records feels like a secret hideaway, a 22-seat wooden sushi bar serving tiny cups of sake and delicate cuts of sea urchin, eel, sea trout and caviar (plates from $7 to $25).

For a glimpse of sumptuous old-world Boston, reinvented for a modern audience, there is nothing quite like Yvonne’s , the dimly lit bar and restaurant that occupies the former Locke-Ober, an iconic Boston restaurant that opened in 1875 and endured for 137 years. Once the exclusive hideaway of bluebloods, the grandly appointed space retains its mysterious glamour, with whimsical touches like the portrait of Bill Murray, dressed in epaulets, that hangs above the fireplace in the library bar, and the smoky drama of the Rubicon, a gin, chartreuse and rosemary cocktail ($16) that is briefly set aflame. This is a room to dress up for, to see and be seen in; just don’t forget to try the lobster ricotta dumplings in black truffle butter ($32) and the seared haloumi with orange-blossom honey and crispy chickpeas ($16).

“The Embrace,” the Common’s newest and most hotly debated public monument, pays tribute to the love between Dr. Martin Luther King Jr. and Coretta Scott King, in the city where they met.

Whatever your level of baseball fandom, a pilgrimage to Fenway Park feels necessary in Boston, whether it’s to watch a Red Sox game or soak up the history of the sport’s oldest, smallest ballpark on a Fenway tour ($25). You’ll get plenty of Yankees trash talk in this hourlong expedition, plus colorful backstories on the Curse of the Bambino and the Green Monster, the towering outfield wall that boasts the oldest manual scoreboard in baseball. If sports aren’t your thing, opt for another neighborhood gem, the Isabella Stewart Gardner Museum , in a Venetian-style palace. Afterward, stroll a half-mile down Brookline Avenue to the Time Out Market , a cavernous food hall stuffed with local favorites, including Cusser’s three-way roast beef sandwich (with BBQ sauce, mayo and cheese, $13) and butter pecan crullers ($5) from Union Square Donuts .

Disneyland for history buffs lies on Beacon Hill, a short ride from Fenway on the MBTA Green Line. Wander through the Granary Burying Ground , established in 1660, a shady oasis beside busy Tremont Street, to pay respects to the founding fathers Samuel Adams, John Hancock and Paul Revere, all of whom are buried here, along the city’s 2.5-mile-long Freedom Trail . Hike uphill past the Massachusetts State House to find the African Meeting House , the country’s oldest surviving Black church building, and the Museum of African American History ($15). Downhill on Charles Street, browse the unusual and beautiful jewelry at December Thieves , and explore Beacon Hill Books & Cafe , a Tasha Tudor illustration come to life with its steep staircases, reading nooks and fireplaces. Afternoon tea is served on Sundays ($65).

No Boston neighborhood has seen more recent transformation than East Boston, or Eastie, long a home to new immigrants and Logan Airport, and now morphing into a trendy waterfront playground. Change has brought parking woes and identity angst , but also a complex vibrancy. A seasonal ferry ($5 round trip) runs every 30 minutes from Long Wharf, near the New England Aquarium, across Boston Harbor to East Boston, or take the M.B.T.A. Blue Line to Maverick station. Stop by Carmella’s Market, an authentic Italian corner store, for oversize meatball or chicken cutlet subs ($10 to $13) and picnic in Piers Park for the stunning skyline views across the harbor.

Boston’s Institute of Contemporary Art , in the Seaport neighborhood, runs a summer outpost in East Boston called the Watershed (free admission), in a former pipe factory. (A water taxi links the two sites .) An exhibition by the British artist Hew Locke, “ The Procession ,” through Sept. 2, explores memory and identity in an installation of 140 life-size sculptures of masked figures. For post-show contemplation, Downeast Cider House Taproom is steps away, offering four-flavor flights ($15). Or, if the wait there is too long, walk 15 minutes to Tea by the Sea , a spacious waterfront cafe with loungy leather couches, jewel-toned velvet footrests and an extensive menu of bubble teas, smoothies and revelatory delights, including mango coconut milk slush (drinks $5 to $10).

For sunset views and lawn party energy, there is Tall Ship , a floating oyster bar moored at East Boston’s Pier One. A lively seasonal venue favored by a youthful crowd, with cornhole, live music and a water shuttle ($4) to other harborfront hot spots, this is not the East Boston of old. But that neighborhood is still here, too. For dinner, try one of its gems: Rincon Limeno , in Day Square, serves Peruvian food in a friendly, unpretentious atmosphere. The ceviche is beloved by locals, but seafood-averse diners will find their own favorites, like the hearty Tacu Tacu ($25), a heaping plate of fried rice-and-bean cake, topped with steak or chicken, perfectly spiced and smothered in sauce. Sip a silky pisco sour on the back patio before catching the train back to your hotel.

People ride a Swan Boat in the Public Garden, adjacent to Boston Common.

The John F. Kennedy Presidential Library and Museum

Begin at Columbia Point in the Dorchester neighborhood, where the soaring white profile of the John F. Kennedy Presidential Library and Museum rises above the blue backdrop of Dorchester Bay. Rent bicycles from the BLUEBikes station in front of the Campus Center at the University of Massachusetts Boston ($10 per day; check bikes before you go to make sure they’re working). Slip behind the J.F.K. library to pick up the Boston Harborwalk , a near-continuous, 43-mile “linear park” that traces the city’s waterfront. Pedal along, listening to the waves, the gulls and the planes descending toward Logan Airport; stop to hunt for shells or shards of sea glass at beaches along the trail.

A ride of about four miles takes you to Castle Island, in South Boston , another oceanfront peninsula with walking trails, beaches and a rich military history; free tours of Fort Independence , which dates back to the 1600s, are offered on weekends. No Castle Island idyll is complete without a stop for sweet and salty sustenance at Sullivan’s , a beloved Southie landmark serving burgers, hot dogs, lobster rolls and ice cream since 1951. A public front porch for the city’s summer nights, the scene is equal parts chaotic and laid-back: children shrieking; dogs chasing balls; planes preparing for landing just above your head. Keep one eye on the sly Southie seagulls, who will dive-bomb your French fries ($3.75) when you least expect it.

Beer arrived on the Mayflower, and helped to fuel the American Revolution, so it’s no surprise to find a bevy of neighborhood breweries in Boston. Drop your bikes at the BLUEBikes station on Day Boulevard and catch an Uber to Dorchester Brewing , with its sunny outdoor deck, Skee-Ball and in-house Museum of Bad Art . Don’t resist the juicy brisket sandwich ($15) from the M&M BBQ counter inside the taproom. (Ask for a fork.) More exotic fare, including jerk jackfruit sliders ($13), is a short walk away at Comfort Kitchen , a Black-owned cafe acclaimed for its globally inspired menu.

Have a weekend to explore a destination? We’ve got the perfect travel itinerary.

Colorado Springs: ​​Colorado’s second-largest city, which brims with outdoor activities , is enticing visitors with a new museum and revamped hotels.

Minneapolis: Springtime is best for exploring this Midwestern city’s lakeside trails, robust arts scene and top-notch restaurants .

Maui: The beauty and hospitality of this Hawaiian island, still recovering from last year’s wildfires, remain as vibrant as ever .

Toronto: Savor the diversity of this lakefront city through its hidden bars, small-but-fascinating museums and vibrant restaurants .

Cape Town: Take a food and storytelling tour, cruise one of the world’s most beautiful coastal drives and see contemporary African art in this city with stunning views in every direction .

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18 Top-Rated Weekend Getaways from Boston

Written by Barbara Radcliffe Rogers Updated Aug 1, 2023 We may earn a commission from affiliate links ( )

With all the attractions in Boston, tourists will always find plenty of things to do. But getting away from the city for a couple of days has its appeal, too, and Boston is perfectly located in the center of New England, within easy reach of the region's best places to visit.

Whether you enjoy outdoor sports, long sand beaches, dinners with an ocean view, island retreats, idyllic small towns, or immersing yourself in nature and mountain scenery, you'll find it within a few hours' drive – or train ride -- from the city.

Plan your next escape with this list of the best weekend getaways from Boston.

1. Portland, Maine

2. provincetown, massachusetts, 3. martha's vineyard, massachusetts, 4. nantucket, massachusetts, 5. old orchard beach, maine, 6. block island, rhode island, 7. berkshires, massachusetts, 8. newport, rhode island, 9. mystic, connecticut, 10. lake winnipesaukee, new hampshire, 11. rockport, massachusetts, 12. kennebunkport, maine, 13. portsmouth, new hampshire, 14. lincoln: gateway to new hampshire's white mountains, 15. providence, rhode island, 16. stowe, vt, 17. old saybrook, connecticut, 18. ski weekend in new hampshire, map of weekend getaways from boston.

Portland has undergone a renaissance of late, becoming a hot spot for travelers looking for a refreshing weekend getaway from Boston. New restaurants are always opening, and their chefs are winning awards. With that in mind, it's a particularly popular spot for those looking for a foodie destination.

This coastal city goes a lot deeper than its remarkable food scene and, depending on your interests, Portland has a little something for everyone. Outdoor enthusiasts can take advantage of a multitude of water sports. Hiking trails surround the area. Art lovers should head to the Portland Museum of Art , where an impressive number of works from both local and international artists are on display.

Step into another world at the Victoria Mansion , the 1800s home of a prosperous family, with an elaborate and remarkably well-preserved period interior. The historic " Old Port " is a cobbled-street neighborhood on the waterfront, with plenty of shops and restaurants, many housed in repurposed warehouses.

Outside the city center, the beaches at Cape Elizabeth are among Maine's best, or you can take a ferry to see the Casco Bay Islands. My favorite day excursion from Portland is the short ferry ride to Peaks Island , where I rent a bicycle or golf cart to circle the rocky shore on the bike path. A stop at the quirky Umbrella Cover Museum near the ferry landing is always a highlight.

For an overnight stay, good value can be found at the Holiday Inn Portland by the Bay , which offers free Wi-Fi and a pool. Directly on the waterfront is the Portland Harbor Hotel , a boutique property with luxury amenities.

Provincetown (P'town to locals) is a vibrant city located at the tip of Cape Cod's "hook." Full of art galleries, ice-cream stores, eclectic shops, and unique murals, this free-spirited town is a one-of-a-kind destination.

The best months to visit are July and August, when the water is at its warmest and the beaches at their most inviting, and it's the time when the town comes alive with tourists of all ages, shapes, and sizes. This is a popular spot in the summer, and it's best to book early if you're hoping to spend a night or two.

The iconic Pilgrim Monument is a landmark you can spot from pretty much everywhere in town, reminding visitors that Cape Cod was the first landing place of the Pilgrims in 1620. A climb to the top rewards visitors with remarkable vistas.

To play in the waters off P'town, you can rent a kayak or paddleboard.

Provincetown is about two and three-quarters hours from Boston, but in the summer, it could take much longer (sometimes four hours or more) to reach your destination. Travel on a weekday (not including Friday) for a faster drive or, better yet, leave the crowds behind by taking a seasonal ferry. Boston Harbor offers ferries that run to Provincetown in only one hour.

For your weekend stay, the Lands End Inn offers luxurious accommodations with majestic views of the Atlantic Ocean and the region's soft, sandy beaches. Additional Provincetown accommodations can be found at the Cape Colony Inn , which has an above-ground pool among its many amenities.

Read More: Top-Rated Things to Do in Provincetown, MA

Martha's Vineyard is the perfect getaway to leave the hustle and bustle of Beantown behind. This island has long been a prized vacation spot for Boston's elite and others just wanting to get away, recharge, or enjoy a romantic couples retreat.

While you are here, rent a bicycle so you can explore the island at your leisure. On the southwestern tip of the island is Aquinnah Cliffs , a popular tourist spot, where you can see the impressive clay cliffs. From the top, you can view the Gay Head Light or the Elizabeth Islands.

Animal lovers should head to Island Alpaca , where you can meet one of the friendly Huacaya alpacas and tour the beautiful farm. The main draw to Martha's Vineyard is the beach, so be sure to enjoy the ocean, sand, and sunshine on your trip.

Martha's Vineyard is a few hours from Boston, but well worth the drive. If you want to bring your car, make sure to have a ferry reservation booked well in advance (we're talking months, not days). You can also reach it via plane. In all, there are six main ways to get from Boston to Martha's Vineyard .

Centrally located in Edgartown, the Vineyard Square Hotel and Suites is a boutique property with modern décor and seaside charm.

Thirty-six miles out to sea, this island off Cape Cod is committed to preserving its past, while keeping its amenities and tourist facilities fresh and up-to-date. Rose-covered cottages, cobblestone streets, and white picket fences are the norm. Many of the roads are unpaved, and a good portion of the island is devoted to conservation land.

Although Nantucket is known for its beaches, culture and history play a big role in the island's appeal. The remoteness and simple beauty add to the abundance of charm.

For just a weekend visit, leave your car at home and rent a bicycle (available right at the ferry landing) to get around and see the island. Stop by the Brandt Point Lighthouse or one of the many pristine beaches like Ladies or Jetties Beach .

A large selection of restaurants offers many choices, but on summer weekends, make sure to have a reservation. You could also load up on the amazing bounty of seafood or readily prepared sandwiches at Bartlett Farm and have a picnic on the beach.

The easiest way to get to Nantucket is to fly from Boston via Cape Air, or you can drive to Hyannis and take the ferry over. It will take a few hours either way, so this getaway is best made on a long weekend.

Most hotels on Nantucket are in town. The Veranda House along with the historical Jared Coffin House are centrally located and within walking distance to the harbor and a wide selection of restaurants in all price ranges. They're known as part of the Nantucket Resort Collection .

Read More: Top-Rated Attractions & Things to Do in Nantucket

Old Orchard Beach is all about fun in the sun, with a rosy tint of nostalgia. Seven miles of beautifully maintained sand is backed by low dunes, and every bit of it is publicly accessed. You can walk to the beach from dozens of low-key family-friendly lodgings.

Best, of all, you can arrive right at the beach by Amtrak's Downeaster train from Boston . The station is a few steps from the long traditional pier, which has extended into the water since 1898, still lined with an array of kiosks, ice cream stands, and eating places. Beside the pier is an attraction even more enticing for kids than the miles of sand: Palace Playland .

The amusement park's Ferris wheel rises from the beach for dizzying ocean and coastal views, and the original carousel wheezes out the same tunes on its calliope that have played there for generations of families. One of those families was mine and some of my most treasured childhood memories are of riding that carousel on hot summer days. More than two dozen rides and activities make New England's only remaining oceanside amusement park as much fun for today's kids as it was for me.

The pier, the somewhat honky-tonk holiday-by-the-sea vibe, the Ferris wheel, the calliope music, the squeals of kids on the Tilt-a-Whirl and miles of golden sand all combine to make Old Orchard head the list of the top beaches in Maine .

Located just off the coast of mainland Rhode Island and Long Island, New York, this nine-square-mile isle is only accessed by ferry from the mainland. Getting here from Boston is easy. Take the hour-and-a-half drive to Kingston and then hop on the Block Island ferry, which takes approximately 15 minutes from port to port.

Once there, rent a moped or bike and explore the 17-mile perimeter where you'll find some of the most pristine sandy beaches in Rhode Island . Even though Block Island is small, it's filled with dozens of charming specialty shops, art galleries, and more.

Nature enthusiasts will enjoy the Clayhead Nature Trail, Rodman's Hollow , and Settlers Rock . Wear sturdy shoes and pack snacks, and plenty of water and sunblock, as you'll want to hit these trails for hours.

At the Block Island Maritime Institute , you'll likely learn something new about the diverse marine life in this area. If you are looking for a little more adventure, try a fishing excursion with Block Island Fishworks .

National Hotel , within walking distance from the ferry docks, is the epitome of a classic Victorian-style hotel. The large structure has a front porch made for rocking chairs and binoculars. Breakfast is included in your stay.

There are few views as beautiful as those from atop the Berkshire Hills. This gorgeous region, one of the most popular getaways from Boston and New York, spans western Massachusetts and parts of Connecticut. It's packed with some of Mother Nature's best creations, a natural wonderland begging to be explored and photographed.

This area offers a lot to those who choose it for a weekend getaway from Boston: visiting quaint towns, eating great food, and hiking lush trails top the list of things to do in the Berkshires . Depending on your mood, you can enjoy relaxing during a class at the world-famous Kripalu Center for Yoga and Health in Stockbridge, or indulge your inner adventurer by white water rafting or flying high through the trees on a zipline. Alternatively, you may simply choose to relax at one of the beautiful resorts in the Berkshires.

Art lovers and avid gardeners will particularly love this area as it's home to the Norman Rockwell Museum , the home and restored gardens of author Edith Wharton, the Berkshires Botanical Garden , and the studio and gardens of America's foremost public sculptor, Daniel Chester French.

In the heart of the Berkshires, the chic Hotel on North is a loft-style boutique hotel, with modern conveniences, exposed brick, and high ceilings. Located in Lee, Black Swan Inn on the Lake is a lakefront property with balcony rooms overlooking the water.

A two-hour drive from Boston , Newport is like no other town in America. Long Bellevue Avenue and surrounding streets are lined with mansions that were the summer palaces of New York's ruling families at the turn of the 20 th century. Fully restored, these dazzle with gilded and painted salons and ballrooms, and sumptuous living areas.

Top on your list to visit should be The Breakers and The Elms , as well as Marble House when it reopens from renovations. You can see several of these (along with ocean views) from the famous Cliff Walk, or from a stroll down Bellevue Avenue.

Its sparkling waterfront views, seafood restaurants, pedestrian shopping areas, and romantic boat cruises are more reasons to visit Newport . Thames St. is the place to browse for restaurants, and art lovers should stop at my favorite museum in Newport, the National Museum of American Illustration, to see murals by Maxfield Parrish and works by other noted illustrators.

An elegant stay reflecting the Gilded Age can be found steps from the Cliff Walk at The Chanler at Cliff Walk . For a fabulous stay across a small inlet near the harbor, select Gurney's Newport Resort and Marina . The in-house restaurant has some of the best views in town.

There are few towns as charming as Mystic, a seaside village about two hours southwest of Boston, and one of the most attractive small towns in Connecticut .

Visiting the Mystic Seaport Museum is one of Mystic's top things to do . At the recreated 19 th -century seafaring village, visitors can board the world's last wooden whaling ship, the Charles W. Morgan , or sail around the harbor on the working catboat, Breck Marshall . Kids will learn seaworthy skills such as knot-tying in the Children's Museum .

Nearby, you'll find the town's other main tourist draw, the Mystic Aquarium . One of the top attractions in Connecticut , this is a mecca for lovers of marine life. Beluga whales, seals, and penguins call this aquarium home.

Across the street lies the lovely Olde Mistick Village . Save your appetite, as it's filled with great restaurants and shops selling everything from candied nuts to homemade donuts to flavored popcorn and fudge.

The Whaler's Inn is a charming place to rest your head at the end of a busy Mystic day. Centrally located and newly renovated, this historic inn has rooms in five buildings, including family-friendly suites. Taber Inn & Suites is another quaint hotel that's been family run since 1971. It boasts an indoor pool, and the luxury suites come with a fireplace, Jacuzzi tub, and private balcony.

New Hampshire's Lakes Region is the freshwater playground of the northeast, and Lake Winnipesaukee (we locals simply call it "the Big Lake") is its best-known and largest body of water.

The small city of Laconia , known for its annual motorcycle rally, sits at the southern end of the Big Lake, and is a great place to get a taste for what the Lakes Region has to offer.

Weirs Beach is Laconia's hot spot, home not only to one of New Hampshire's most popular beaches , but also a wide, boardwalk-style waterside stretch with open-air arcades, shopping, and restaurants. It's also a port for the historic cruise boat, M/S Mount Washington and the mail boat Sophie C., America's oldest floating post office, both excellent ways to get out on the water and enjoy the scenery.

Many regular visitors bring their boat for the summer, but you'll find several marinas that offer rentals. The best part of boating on the Big Lake is pulling up to the dock at a restaurant – both my favorites are on the water in Meredith. Town Docks Restaurant is my spot for an informal bite and Lago the perfect stop for a romantic meal.

For a scenic ride on land, hop aboard the Winnipesaukee Scenic Railroad right at the dock.

Whether by boat or by car, exploring the small towns along the shores of Winnipesaukee is a great way to spend an afternoon. While Meredith is a bit bougie, towns like Center Harbor and Wolfeboro are more down-to-earth, offering plenty of shops and scenic spots for tourists to enjoy.

Author's Tip: If you're not a fan of motorcycles in droves, avoid the Laconia area during the end of June; Bike Week takes place over nine days, typically ending on Father's Day. If you do visit then, expect restaurants to be packed and hotel rates much higher than average.

You'll understand at once why Rockport has long been a haven for artists. The waterfront, with its boats and cluster of fishing shacks simply begs to be sketched, photographed, or painted. Right in the center of every harbor view is the iconic Motif #1 , a fishing shack that has been made famous by decades of artists and photographers.

One of the most charming small towns in Massachusetts , this seaside retreat lies an hour northeast of Boston, right on the tip of Cape Ann, where it meets Sandy Bay. Beside the harbor is Bearskin Neck , filled with quirky shops, restaurants, and art galleries.

For ocean views and walks along the shore, follow the somewhat rough coastal path or drive to Halibut Point State Park , a former granite quarry with a lighthouse and ocean views.

Pack a swimsuit and towel, as you may want to spend time on the beaches between browsing in galleries, exploring the waterfront parks and taking a whale-watch cruise from the nearby fishing port of Gloucester.

Head back to The Seafarer Inn if you're hoping for a laid-back waterfront hotel that oozes charm. The Rockport Inn and Suites is another good place to stay if you're in the market for a slightly larger, more upscale, family-friendly spot with extra amenities, like an indoor pool and hot tub.

If you're looking for an upscale coastal retreat, you'll be happy you traveled to the little town of Kennebunkport in Maine. A bustling locale in the summer, this popular vacation spot is a two-hour drive north of Boston via Route I-95. Unlike much of Maine's rocky coastline, Kennebunkport has several long sandy beaches and a convenient transport system to get you to the sand without a car.

One of the best ways to see Kennebunkport and learn about its rich history is the Intown Trolley Tour . You'll get a full rundown of the notable attractions, from the Bush compound to the Spouting Rock and a local monastery. Take a cruise to see lighthouses, or drive to York for close-up views of Maine's most beautiful, Nubble Light, on its wave-swept island.

Around Dock Square you will find your fill of unique boutiques, restaurants, and art galleries. The town does a good job of incorporating festivals into the shoulder seasons, making the Kennebunks a good year-round destination. The month of December is especially festive, with sleigh rides and the town Christmas Tree decorated in colorful lobster buoys.

The Nonantum Resort offers plenty of additional activities on their menu, family fun, and an on-site lighthouse. The Rhumb Line Resort offers great value with an in-ground pool and free breakfast and Wi-Fi.

Portsmouth's elegant beauty and lively maritime air are a winning combination. Add a food scene that garners national attention, and you'll see why this port city is a popular getaway.

Learn more about the area and its history with a visit to the open-air Strawbery Banke Museum . Here, costumed docents help visitors understand what it was like to live and work in the waterfront neighborhood over the past several hundred years.

In addition to the buildings you can tour here, Portsmouth is fortunate to have many more homes from the Colonial and Federal periods that are in original condition and open to visitors. Foremost of these are the Warner House and the Moffatt-Lad House , which also has a restored Colonial garden.

But Portsmouth's attractions are not all about its well-preserved past. Highlighting the arts and culture scene is The Music Hall , with a full schedule of live theater, Broadway shows, and top-performer appearances.

Market Street is aptly named, lined with boutiques, galleries, and locally owned shops set in historic brick mercantile buildings. For a look at Portsmouth from the sea and a chance to see its lighthouses, take a harbor cruise or a trip to the Isles of Shoals.

Author's Note: My favorite time to go to Portsmouth is in the late spring when trees and flower gardens are in bloom at the harborside Prescott Park. In the summer the park is a venue for concerts.

Along with its waterfront location, the free breakfast and a pool are added inducements to stay at Hampton Inn & Suites Portsmouth Downtown . Those looking for a New England bed-and-breakfast experience will find the Sailmaker's House a great choice.

Just over two hours from Boston on I-93, Lincoln is a convenient gateway to both sides of the White Mountains. Immediately north are the scenic and natural wonders of Franconia Notch , and to the east, the lofty Kancamagus Pass leads to the resorts and attractions of North Conway and the Mt. Washington Valley.

In the heart of the White Mountains region, a base in Lincoln allows you to enjoy some of the state's most beautiful scenery and exciting attractions without an exhausting drive. Lincoln's accessibility and abundance of things to do for all ages and interests make it as perfect for a romantic getaway as for a family weekend romp; outdoor enthusiasts have plenty of options, too.

If you're taking a summer break with grade-school kids, your first stop should be Clark's Bears . This amusement park may be on the smaller side, but its diversions are not the same-old thrill rides. The bear shows — these animals were rescued as orphans by the Clark family and given a loving home here -- show how clever those giant furballs really are.

If the weather is warm, Whale's Tail Water Park is nearby, offering everything from gentle kiddie pools to surfing and bodyboarding lessons. Another big hit is the Hobo Railroad , where an 80-minute train ride departs rain or shine from May through October.

Couples can have a romantic five-course dinner aboard the Café Lafayette Dinner Train on a 20-mile rail adventure in their chrome-adorned 1950s-style dining cars.

The Loon Mountain Gondola and the Cannon Mountain Aerial Tramway lead to mountaintop vistas that are glorious, especially when painted with autumn foliage.

Author's Tip: Make your first stop the Gateway Visitor Center, conveniently located right at the exit 32 off-ramp. Along with getting information about attractions in the region, you can take a selfie with a real (stuffed) moose.

Read More: Best Things to Do in Lincoln, NH

Providence lies about an hour's drive from Boston. This small city is busting at the seams with charm and a rich history, making it a wonderful and very romantic spot to spend a weekend getaway from Beantown.

Rising above the downtown area (called DownCity here) is the Rhode Island State House, with the fourth-largest self-supporting marble dome in the world. Below, a river that once flowed beneath the pavement, has been uncovered, crossed by small bridges that give it the feel of a Venetian canal.

Reserve ahead to complete the scene with a ride in an authentic Venetian gondola. Reserve WAY ahead to ride during one of the summer WaterFire evenings, when the river is filled with bonfires.

Above the downtown area, The Hill is crowned by the campus of the Ivy League Brown University . Below it, the streets are a delight to stroll, past the fine old homes and well-kept dooryard gardens. The finest of these line Benefit Street, known as The Mile of History . You can tour the imposing John Brown House.

If you are an art lover, the Rhode Island School of Design Museum of Art has an impressive body of work on display. More than 90,000 pieces of art range from ancient Egyptian and Asian works to cutting-edge contemporary designs. Check the schedule for upcoming shows at the Providence Performing Arts Center .

If you're traveling with your family, take the kids to the Roger Williams Park Zoo , one of the country's finest. Small, but filled with hands-on experiences, the Rhode Island Children's Museum is easy to spot by the big green dragon looking down from the roof.

Providence Marriott Downtown has a resort-type atmosphere and a great outdoor pool. It's also one of the few places in town to offer free parking. In the heart of downtown, The Dean Hotel has been tastefully restored to reflect its past and is convenient to the Convention Center.

• Read More: Top-Rated Attractions & Things to Do in Providence, Rhode Island

While most think of Stowe as a winter destination, an upscale Vermont ski resort , and a haven for skiers and snowboarders, this classic Vermont small town is captivating at all times of the year. During fall, Stowe is at its most photogenic, with vibrant hues of red, orange, and yellow painting the landscape; in summer it abounds with outdoor activities.

For those traveling from Boston, the drive to Stowe takes about three hours . Once there, lucky weekenders can hike mountain trails, enjoy a latte in a cute café, or shop in one of the several galleries showing the works of local artists and craftspeople.

One of the top things to do in Stowe is hike or bike the Stowe Recreation Path , a paved 5.3-mile trail from the center of the village to just below Mt. Mansfield. Open all year, the path is wide enough for walkers, joggers, and cyclists, to enjoy it at the same time; it's groomed in the winter for Nordic skiers.

The Trapp Family Lodge is set within a European-style alpine resort on a sprawling 2,500 acres of incredible landscape. The Lodge at Spruce Peak is another fab spot to rest your weary heads. Also set within a phenomenal mountainous terrain, this lavish spot is the only ski-in, ski-out luxury resort in Stowe.

The small seaside town of Old Saybrook is about 125 miles southwest of Boston, and one of the best places to visit in Connecticut . Among the state's oldest towns, Old Saybrook bursts with charm, especially in the Fenwick Historic District , where you'll find picture-perfect shingled cottages that date to the 19 th and early 20 th centuries.

It was once the home of famed actor, Katherine Hepburn, and you can catch a concert, comedy show, or film at The Kate , a cultural arts center named in her honor. Visiting the Florence Griswold Museum is another top thing to do in Old Saybrook . Technically five minutes outside the border, in neighboring Old Lyme , this bright yellow house is impossible to miss.

Harvey's Beach is one of the top beaches in the state , and the reason that Old Saybrook tops the list of Connecticut's best beach towns . Spanning 100 yards of shoreline, this is a highly popular spot for summertime fun with its fine sand and calm water.

The Saybrook Point Resort & Marina is by far the best place to stay in Old Saybrook. Not only does it offer the most stunning panoramic vistas, but the rooms are elegant and there are vacation villas on-site if you're visiting with a larger group. The Lighthouse Suite is a romantic spot set in a lighthouse (obviously) at the end of the pier.

Thanks to I-93, it's an almost straight shot from the Boston metro area to many of New Hampshire's best ski mountains. Gunstock Mountain Resort , located right by Lake Winnipesaukee in Gilford, is just under two hours' drive from Boston.

This county-owned ski area is known for reasonable lift prices and several money-saving pass options, offering 55 trails as well as tubing, ziplining, and a Mountain Coaster.

Waterville Valley Resort is about 15 minutes from Exit 28. This full-service resort is its own little community with plenty of things to do if you don't want to ski its 50+ trails, including ice skating, sleigh rides, and lots of other activities.

Deeper in the legendary White Mountains, Loon Mountain is less than 10 minutes from the highway and just over two hours from Boston. With three peaks and great snowmaking power, the resort offers 61 trails with 2,100 feet of vertical drop, plus a good variety of terrain parks, on-slope lodging, and other winter activities that include skating, tubing, and even winter ziplining.

Cannon Mountain is just a few minutes north of Loon, and although this state-park-run hill doesn't have the full resort amenities of its neighbor, it is known for its challenging, steep terrain with 81 trails accessed by 10 lifts.

Author's Tip: If you're looking for a quick and inexpensive ski getaway, head to the smaller Pats Peak in Henniker, just 90 minutes from Boston. You can even get here without a car thanks to the Ski Bus. You'll get a discount on lift tickets when you take the bus, but lifts are surprisingly affordable no matter how you get there. A good mountain for families, Pat's Peak has an excellent rental shop on-site and a full range of runs for all skill levels.

Read More: Top-Rated Ski Resorts in New Hampshire

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The 16 best day trips from Boston

Take a break from city life and visit these nearby New England destinations—no packing required

Photograph: Courtesy Visit Maine

While many of us could easily spend every waking moment in Boston, it can be refreshing to escape the city for 24 hours or so. Fortunately, this picturesque New England region offers an array of potential day trips from Boston, including quaint seaside villages, historic towns and stunning mountain vistas. So grab your pals or significant other, and hop on a ferry, train or automobile to one of these lovely destinations. Once you're back in town, you'll once again feel ready to take advantage of the  best Boston attractions ,  best free things to do in Boston  and  best museums in Boston . And when you need a little longer time away check out our list of the best weekend getaways in New England . RECOMMENDED: The Best Hotels in Boston

Been there, done that? Think again, my friend.

Best day trips from Boston

1.  newport, ri.

The Newport mansions of the Gilded Age still impress with their grandeur—just as they were built to do. If you have time to only tour one estate, check out The Breakers . Near the International Tennis Hall of Fame , the Audrain Auto Museum houses a seasonally rotating display of incredible cars inside a gorgeous Art Deco building.

Take the Cliff Walk, which has stunning views of the ocean, or relax at the public Easton’s Beach . Stroll past cool shops and eateries on narrow Thames Street. On Marlborough Street, dine at the White Horse Tavern , which claims to be America’s oldest restaurant, or duck over to The Reef at Howard Wharf for dinner and drinks with a view. Near the harbor, Bowen’s Wharf’s buildings date back to the 1700s, now offering an inviting maze of restaurants and shops. Stroll over the causeway to Goat Island where the Newport Harbor Lighthouse is overlooked by the upscale Gurney’s Resort.

2.  Portland, ME

​​Maine's largest city, located about a two-hour drive north of Boston, attracts epicureans from around the country to its cobblestone streets. Wander the charming, hilly Old Port district, where every kind of boutique imaginable touts colorful wares. Pop into one of the many quaint pubs and dimly lit cocktail bars, like the excellent Jewel Box or Blyth & Burrows —the latter of which pairs the best in innovative mixology with equally scrumptious small plates. In the West End arts district, enjoy the I.M. Pei-designed Portland Museum of Art and the State Theatre , which hosts national acts, both musical, comedic and theatrical.

The food scene here lives up to the hype:   Cong Tu Bot for nationally celebrated Vietnamese fare;  Green Elephant for an inventive vegetarian meal;   Evo Kitchen + Bar for progressive twists on Mediterranean cooking; or  Union , a vibrant locavore haunt located at  The Press Hotel , whose historic building was formerly the home of the Portland Press Herald.

3.  Newburyport, MA

The Newburyport Historic District, which encompasses most of the downtown, is listed in the National Register of Historic Places. This treasure trove of well-preserved, Federal-period architecture includes the notable Cushing House Museum & Garden , home of statesman Caleb Cushing, and the Custom House Maritime Museum , which also unravels local history. The beautiful Waterfront Park and boardwalk has regular concerts during warmer months.

Catch a play or see a show at the Firehouse Center for the Arts , grab a gourmet sandwich and bottle of wine at Joppa Fine Foods ,  relax with excellent cocktails and modern Middle Eastern bites at Bar25 ,  dine on classic seafood at The Black Cow  or head to the Newburyport Brewing Company ,  offering a friendly tap room and beer garden.

Newburyport includes part of neighboring, sedate Plum Island , a barrier island overlooking salt marshes.

4.  Gloucester, MA

Shipbuilders and fishermen put Gloucester on the map, and both industries still exist there today —just  on a smaller scale. The Fishermen’s Memorial on Gloucester Harbor honors all those lost at sea, including the Andrea Gale and its crew, the real-life victims of The Perfect Storm . Check out the Cape Ann Museum , which has an amazing collection of art and artifacts specific to Gloucester and its surroundings.

Across narrow Main Street, you can savor straight-off-the boat seafood at the chic basement restaurant  Tonno . Oak to Ember  will impress with its menu of hearty, wood-fire-cooked dishes and thoughtful cocktails. Or, if you're more about ocean views, head to the Beauport Hotel , whose 1606 Restaurant has a great deck overlooking the water. Next door to the hotel, Beauport Cruise Lines offers seasonal jaunts around the harbor.

5.  Salem, MA

Salem is forever linked to its horrifying and fascinating 1692 Witch Trials. The curious flock to the home of presiding Judge Corwin, which today is a museum known as The Witch House . Halloween is a big thing here—so are new age and cult shops. On a less spooky note, the Peabody Essex Museum houses a wonderful art collection, and Salem is the birthplace of Nathaniel Hawthorne, author of The House of the Seven Gables. You can even tour the house he may have been writing about, the 350-year-old Turner-Ingersoll Mansion.

Though it only dates back to 1930, Pioneer Village —a 10-minute drive from downtown, in Forest River Park—reenacts early 17th-century colonial life. Eat like a local at Ledger or Settler , or nerd out with old school arcade games and pinball machines at Bit Bar . 

6.  Provincetown, MA

Creative, sassy P-Town—located only a 90-minute ferry ride from Boston—is an artsy LGBT hotspot. It’s got a great mix of galleries, restaurants and nightlife hangouts. Lined with dozens of colorful shops, friendly eateries and local businesses, Commercial Street is the bustling heart of the town. Seek out one of the many events and festivals that fuel the thriving arts scene.

The famous and seasonal  Lobster Pot is the biggest name in town for classic lobster rolls and fresh seafood treats. Climb the 252-foot granite Pilgrim Monument for dramatic harbor views, then escape to Race Point Beach to enjoy the sights, sounds and smells of the open ocean.

Eat innovative seasonal dishes at Strangers & Saints and great seafood at Mac’s Fish House , which has crispy fish and chips and Happy Hour dollar oysters. Explore the beautifully barren Outer Cape’s stretch of the Cape Cod National Seashore , including Truro’s picturesque Highland Light .

7.  Ogunquit, ME

Set on the breathtaking Maine coast, Ogunquit is a popular, classic beach town with a quiet ambiance, particularly in the cooler months when crowds disappear. But it’s also a historic arts community; the Ogunquit Museum of American Art was started in the 1950s by native artist Henry Strater, a student of Ogunquit’s Perkins Cove artists colony.

Wander the galleries around town, explore the Barn Gallery on Shore Road and get tickets to a show at the Ogunquit Playhouse —which boasts eight decades of professional theatre and summertime children’s productions—or another summer stock theater.

8.  Watch Hill, RI

A coastal village that’s part of the town of Westerly, Watch Hill has one of the best beaches on the East Coast, and celebrity glamour to spare. Get to town early and take a walk out on the Napatree Point Conservation Area , where  you’ll find the remains of Fort Mansfield and lots of beautiful birds like osprey and piping plovers.

After your nature walk, head into the charming town for a stroll and some shopping. The kids will love the vintage carousel, and be sure to have lunch at the Olympia Tea Room (supposedly Taylor Swift’s fave—you can take a peek at her house from afar, too, because it’s hard to miss). Finish the day with cocktails at the gorgeous Ocean House , where you can have a drink and a bite to eat.

9.  Concord, MA

Stroll to the Old North Bridge and explore the Minute Man National Historical Park’s five-mile Battle Road Trail, dedicated to the Battle of Concord (April 19, 1775), where militia engaged with British troops and ignited the Revolutionary War. The 19th-century Transcendentalist movement and its influential authors and thinkers—Ralph Waldo Emerson, Henry David Thoreau and Bronson Alcott—were rooted in Concord, and the Concord Museum is a good place to connect the dots. Located just outside of Concord Center are Walden Pond , which honors Thoreau’s famed naturalist journal, and Orchard House , where Louisa May Alcott wrote Little Women 150 years ago.

Pick up a picnic lunch at The Concord Cheese Shop . The Saltbox Kitchen’s tasty dishes and small-batch brewery are both fueled by produce from its nearby Saltbox Farm. For dinner, Woods Hill Table  also sources from their own farm at Woods Hill in Bath, NH, and the sleek, seasonally-focused 80 Thoreau is worth the day trip alone.

10.  Providence, RI

Providence is a foodie’s dream. Why does this small capital city have so much kitchen talent? Nearby Johnson & Wales University’s College of Culinary Arts is a major factor. Hemenway’s downtown is the grand dame of area seafood restaurants;  Waterman Grille is a vibrant jewel on the East Side near Brown University; and Aleppo Sweets is a lauded Syrian bakery and cafe—just to name a few spots. Federal Hill, the city’s impressive Italian neighborhood, is also loaded with Italian eateries and shops. 

Waterplace Park is a lovely gathering spot, and it anchors the city’s annual WaterFire program, which runs from spring through late fall; braziers along the Providence River are lit at sunset and stoked with aromatic wood by black-clad figures on boats, while themed music plays.

Providence is home to the notable Trinity Repertory Company , and The Strand Ballroom & Theatre, one of the nation’s best rock venues. The Rhode Island School of Design’s museum includes one the country’s finest university art collections.

11.  Mystic, CT

Settled in 1654, Mystic was once a shipbuilding seaport village. Now, it's a quintessential New England town, packed with mom-and-pop shops and activities for the whole family to do. 

During warm weather, spend a few hours on the sea with a day sail or sunset cruise from Argia Mystic Cruises , or visit the famous Mystic Aquarium or the Mystic Seaport Museum .  

After working up an appetite, stroll through the village to see the famous weighted Bascule bridge . P ick up a sweet treat from award winning Sift Bake Shop  and  splurge on a Connecticut lobster roll at the The Shipwright's Daughter  or a hearty, grass-fed burger at the Engine Room .  And, if you must eat pizza in Mystic, head to Nana’s Bakery and Pizza for inventive takes on personal pies.

12.  Falmouth, MA

Falmouth is nestled on the southwestern part of Cape Cod, 20 miles south of the Sagamore Bridge. Lined with great beaches, cool boutiques and relaxing spots to eat and drink, it's also one of The Cape’s easiest towns to get to. Do breakfast or lunch like a local at The Pickle Jar Kitchen .

The Falmouth Museums on the Green brings 1700s Cape Cod to life; the Federalist home of Dr. Francis Wicks is wonderfully preserved and packed with original artifacts. The Shining Sea Bike Trail ,  which hugs the coast and brings you past lovely views of both the Vineyard Sound and Buzzards Bay, runs from Falmouth to Woods Hole. The trail’s name comes from “America the Beautiful,” the famous poem by Katherine Lee Bates, a Falmouth native. (Though once a railroad, the path follows ancient Wampanoag Indian trails.) One more highlight: the Woods Hole Oceanographic Institution Ocean Science Discovery Center .

13.  Lexington, MA

The best part of taking a day trip to Lexington? You can easily do it by bicycle by traveling down the Minuteman Bikeway , which begins in North Cambridge and runs right through the leafy suburb, some 15 miles northwest of Boston. This posh town is most famous for its historic Battle Green , where the bloody Battle of Lexington took place and patriotic Minute Men engaged the British Army on Lexington Common. Many of the original homes flanking the battleground are preserved, including one that serves as a visitor’s center.

Stroll Lexington Center’s mom-and-pop shops, enjoy homemade ice cream at Rancatore’s or dine at il Casale   from local chef Dante de Magistris, who draws from his family’s roots to make handmade pastas, delicious sfizis and classic dishes, all in a rustic-chic atmosphere. For an elegant Sunday brunch or dinner, The Inn at Hastings Park’s Town Meeting Bistro  is a modern pleasure involving sleek, seasonal dishes.

14.  Kittery, ME

Kittery, while most famous for its shopping, has so much more to offer. First stop: Bob’s Clam Hut , a 60-year-old roadside diner that serves incredible fried clams, sustainable local fish and amazing milkshakes. Next stop? Yes, shopping at the adjacent Kittery Premium Outlets , whose stores include everything from discounted Calvin Klein to Lindt chocolate.

Also known for the historic Portsmouth Naval Yard —which is in Kittery, not neighboring Portsmouth, NH—this sleepy town includes Tributary Brewing Company , which has a cool tasting room and live music on weekends.

The heart of Kittery Foreside, which is the downtown area, is Wallingford Square and it's dotted with all kinds of restaurants including the sleek bistro Anneke Jans  and casual asian eatery  Anju Noodle Bar . Or  stop by Lil’s Café , a quaint spot set in a former bank whose old walk-in safe is now its Vinyl Vault, a small alcove with used records for sale. Lil’s bakery downstairs turns out some of the best pastries in New England and excellent chai, too.

15.  Washington, CT

For a small town in rural Connecticut, Washington has a big reputation for its arts and architecture. The Judy Black Memorial Park and Gardens is set in a once-abandoned gas station and boasts lovely landscaping and revolving art exhibits.

Every July, the Litchfield Jazz Festival takes place at venues around town and world-renowned modern dance company Pilobolus holds its Five Senses Festival . In September, Gilmore Girls fans take over—the town inspired the beloved TV program’s fictional Stars Hollow. Surrounded by colonial architecture, you can shop at unique boutiques and treat yourself to dinner (and a room, for a real spurge) at the historic, luxurious Mayflower Inn .

16.  Stockbridge, MA

Just off I-90, Stockbridge is the gateway to the beautiful Berkshires, part of the Taconic Mountains. Main Street is home to the venerable Red Lion Inn , a one-time frontier town tavern that maintains a casual eatery called Widow Bingham’s Tavern, as well as a gorgeously original main dining room with traditional favorites and an award-winning wine list.

Nature and art dominate the area: Just off Park Street, behind Main Street, take the wooden footbridge and walk the Laurel Hill Association’s beautiful trails. Visit the Norman Rockwell Museum and see where the renowned illustrator and artist lived and worked. Nearby, visit Chesterwood , the home of the Lincoln Memorial sculptor Daniel Chester French, and Naumkeag , a Gilded Age architectural masterpiece. A few miles away in Lenox is the Tanglewood Music Center , the Boston Symphony Orchestra’s summer home. Nearby, you can take a guided tour of Edith Wharton’s home, The Mount , and learn about the woman behind the building and the books.

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22 Long Weekend Getaways From Boston

From day trips to weekend getaways, our biweekly traveler newsletter shows you the best of new england and beyond..

Edited by Brittany Jasnoff

Cruising Lake George at the Sagamore Resort. / Photo courtesy of Sagamore Resort

There are 22 weekends left until 2021 is behind us—which means 22 opportunities to hightail it out of town. From New Jersey to Maine, golfing to rock climbing, and everything in between, we’ve rounded up the perfect number of must-do long weekends to take you from the end of summer all the way through New Year’s Eve. So make your reservations and pack your bags: You have 72 hours to recharge. Ready, set, go!

Off-the-Grid Resorts

Food & drink.

Turning Stone’s flagship Atunyote golf course. / Photo by Omar Rawlings

Turning Stone Resort Casino

Verona, New York

Drive Time from Boston 4 hours, 30 minutes

When it comes to golf destinations, there’s no question that Turning Stone should be near the top of any player’s bucket list—and luckily, you don’t have to travel far (or stay long) to get your swing at it. Located in the Mohawk Valley just 30 miles east of Syracuse, the property offers more golf than any other resort casino in the country—but for those sweeping open spaces that upstate New York does so well, you’ll want to hit the flagship Tom Fazio–designed Atunyote course, which has hosted the PGA Professional National Championship multiple times. Listen to babbling brooks, take in the gently rolling hills, and follow in the footsteps of the greats while you’re here—Tiger Woods, Matt Kuchar, Steve Flesch, and Camilo Villegas have all played the Atunyote. Once you’ve ticked that off your to-do list, there are still the Shenendoah and Kaluhyat courses—a little more approachable in terms of difficulty but no less impressive when it comes to scenery.

After a day on the links, spend your night unwinding at any of Turning Stone’s many dining and entertainment venues. It’s hard to beat a sunset reservation at TS Steakhouse for dinner. Located atop the resort’s Tower Hotel, the award-­winning restaurant boasts expansive views in every direction. There are several options for sleeping while you’re here, but we suggest the Lodge at Turning Stone, situated away from the casino’s hustle and bustle—and, more important, just steps from the Shenendoah and Kaluhyat courses. —Todd Plummer

Courtesy photo

3 More Golf Getaways

1 Golf at Bretton Woods Bretton Woods, New Hampshire

Drive Time from Boston 2 hours, 30 minutes

Turns out the White Mountains aren’t just for skiers: During the warmer months, take your golf game to new heights on the two courses abutting Omni Mount Washington Resort. Start on the Mount Pleasant Course—with just nine challenging holes, it’s a suitable warm-up or an ideal choice if you only have a half day to hit the links. When you’re ready for the main event, book a tee time for the 18-hole Mount Washington Course. Not only are the views of the White Mountains breathtaking (especially timed with fall foliage), but you’ll have at your fingertips everything this iconic Omni—which recently added a new wing—has to offer. Pro tip: Be sure to take advantage of the enormous spa. — T.P.

2 Point Sebago Golf Course Casco, Maine

Sparkling lakes, green fields, white birch forests, and perhaps the occasional black bear or two—Maine’s picture-perfect Point Sebago Golf Course is considered one of the finest in the state. Set on 500 manicured acres, this par-72 18-holer is suitable for golfers of all levels. Opt for the Stay & Play package with Point Sebago Resort and you can even snag a well-appointed vacation home for as little as $125 a night—or go for the true Maine experience and book a campsite from just $55. —T.P.

3 Ocean Edge Resort & Golf Club Brewster

Drive Time from Boston 1 hour, 45 minutes

Sorry to twist your arm, but you’ll just have to book a room to play here—the Jack Nicklaus–designed course at this popular Lower Cape resort is available only to guests and golf-club members. Once you unpack your clubs, expect complicated doglegs, dramatic elevation changes, and tough approaches. Sure, it’s a challenging course, but when you get to unwind at the 19th hole with a sunset cocktail on the terrace—or better yet, down at the beach bar—it’ll be impossible not to kick back and let loose a little. —T.P.

The seaside cliffs of Mohegan Bluffs. / Photo courtesy of Block Island Tourism Council

Block Island

Rhode Island

Travel Time from Boston 3 hours

Magical views, gourmet meals, and mopeds: While this island measures only 7 miles long and 3 miles wide, there are more ways than ever to pack a long weekend with beachy fun. First, disembark after the 30-minute high-speed ferry ride from Point Judith in Narragansett and feast your eyes upon the 19th-century Victorian that is the Block Island Beach House. Steps from the dock, the recently revamped hotel debuted 15 new coastal-chic rooms and group-friendly suites this year, plus the island’s only hotel pool. Inside, you’ll find original Block Island artwork in every room; outside, the sprawling covered porch—part of the hotel restaurant, the Surf—offers a clambake on the menu every day.

A sandy path on Block Island. / Photo by Jack Parrott/Getty Images

Crescent Beach, one of the island’s most picturesque stretches, is a short walk from the hotel, though you’ll want to make sure to rent a bicycle (or a moped) at some point and pedal down to Mohegan Bluffs. There, jaw-dropping seaside cliffs, 141 steps down to the water, and a Gothic Revival–style brick lighthouse circa 1874 await. When it comes time to eat, explorers with an appetite will relish the fresh clam strips and seafood nachos at the Beachead. Those who prefer to rinse off the salt before a night out should reserve a table at Restaurant 1879 at the Atlantic Inn, where you can start with spicy watermelon gazpacho, tuck into citrus-and-white-wine-poached lobster on a bed of squid-ink orecchiette, and finish with the chocolate torte, a duck-fat-infused chocolate cake with peanut butter ganache, candied peanuts, and cardamom Chantilly cream. A sweet ending to a sweet trip, you bet. —Madeline Bilis

Photo by Peter Frank Edwards

3 More Island Getaways

1 Chebeague Island Maine

Travel Time from Boston 2 hours, 15 minutes

One of the most easily accessible Maine islands (it’s just 15 minutes from Yarmouth via a painless ferry ride), Chebeague still feels like a throwback to simpler times. Exhibit A: The little town’s only hotel, Chebeague Island Inn, is the stuff of New England summer dreams, with a wraparound porch, a great room complete with a fireplace and board games, and a restaurant that receives its fresh lobster direct from local fishermen each day. Have the hotel shuttle you up—or borrow a house bike for the 3-mile journey—to the scenic, secluded Indian Point Beach, where you’re likely to have the sandy expanse all to yourself. —T.P

Photo by Danita Delimont/Alamy Stock Photo

2 Île d’Orléans Quebec, Canada*

Travel Time from Boston 6 hours, 30 minutes

Natural beauty—not to mention succulent produce—abounds in this storybook setting smack in the middle of the St. Lawrence River, just a short ride over the bridge from Quebec City. Start by picking your own raspberries, strawberries, and blueberries at a farm called L’Arc-en-ciel du Paradis, or the Rainbow of Paradise. As the sun sets, venture to Isle de Bacchus, one of the area’s beloved vineyards, to sip on a sweet glass of ice wine. While the island is dotted with adorable inns, the ultra-cozy La Suite du Quai offers proximity to the lavender fields at the botanical garden La Seigneurie de l’Île d’Orléans (pictured below). —M.B.

3 Shelter Island New York

Travel Time from Boston 4 hours

A hop, skip, and two quick ferry rides away from New London via Orient, the Northeast’s best-kept secret is more than worth the trip for the sprawling beaches, exceptional food and wine, and rambling nature trails with none of the crowds (or turned-up noses) you’ll find elsewhere on Long Island’s East End. Drop your bags at the Chequit, a fully restored 150-year-old inn, take a stroll through the 2,350-acre Mashomack Preserve, then head straight to Sunset Beach in time for waterfront drinks. Dinner at Vine Street Café is a must thanks to an Ina Garten–endorsed Bolognese that’s one of the best you’ll find this side of Italy.  —T.P.

*Be sure to check travel restrictions before booking your trip.

The grand Sagamore Resort feels a world apart. / Photo courtesy of the Sagamore Resort

The Sagamore Resort

Bolton Landing, New York

Drive Time from Boston 3 hours, 45 minutes

How’s this for off-grid? Built in 1883, this sprawling Victorian-style resort occupies its own private island on Lake George. Don’t worry, you can still drive there via a small bridge—but a guard house at the entrance ensures that pesky day-trippers are kept at bay. Once you ditch your car and check in, there’s really no reason to cross back over to the real world. This is, after all, the kind of old-school place that has just about everything you want in a getaway: rooms with private patios featuring Adirondack rocking chairs; eight restaurants and bars ranging from fine dining to a casual pub; indoor and outdoor pools and hot tubs; an 18-hole golf course; a spa and salon offering everything from sports massages to mani-pedis; and splendid Adirondacks views all around. You can choose to do it all, or you can choose to simply sit back in a lounge chair and soak up the sun bouncing off the water.

While there’s plenty for grownups to enjoy, the Sagamore is the kind of magical escape the little ones will love exploring, too—including at an adorable rec center where they can play Wiffle Ball and mini golf and meet new friends at the kids’ club. Once everyone has chosen their respective adventure, the whole family can reunite in time for a sunset cruise aboard the hotel’s touring boat, which offers scenic rides around Lake George. —T.P.

Biking at Twin Farms in Vermont. / Photo courtesy of Twin Farms

Photo courtesy of Twin Farms

3 More Off-the-Grid Getaways

1 Twin Farms Barnard, Vermont

Drive Time from Boston 2 hours, 45 minutes

Could there be anything more romantic than a private mountaintop dinner for two—and only two? At Twin Farms, spread over 300 acres of rolling farmland and forest, you can savor locally grown greens and crispy pork belly in a refurbished ski gondola situated atop the property’s private ski slope. The new dining experience isn’t the only thing you’ll love about this luxe all-inclusive. Whether you’re craving some hard-to-find Heady Topper beer for your room’s mini fridge, an afternoon of guided fly-fishing on one of the farm’s private streams, or a picnic-style lunch down by Copper Pond, your every wish is Twin Farms’ command. —T.P.

Photo courtesy of Chapin Estate

2 Chatwal Lodge

White Lake, New York

The sister to one of Manhattan’s top boutique properties, the soon-to-open Chatwal Lodge is less like a hotel and more like your fanciest friend’s country estate in the Catskills. Accommodations will include 10 suites with private patios overlooking the placid Toronto Reservoir Lake; an 850-square-foot glamping tent; and—if you really want to splurge—a treehouse floating 25 feet above the ground. You’ll have your pick of unplugged activities while you’re here, too, from kayaking to picnicking on the grounds. —T.P.

3 Miraval Berkshires Lenox

Drive Time from Boston 2 hours

Think of this recently opened, all-inclusive Berkshires retreat as a break-glass-in-case-of-emergency option if you need a serious wellness reset. Check in and choose from demonstrations and lectures offered by world-renowned nutritionists, spiritual healers, and more, plus more than 20 different types of yoga and meditation classes. Then unwind in the sublime spa or with a meal emphasizing local ingredients and healthy, mindful eating. You’ll be saying namaste in no time. —T.P.

Riding the waves in York Beach. / Photo by Jay Arbelo

York Beach, Maine

Drive Time from Boston 1 hour, 15 minutes

New England is well known among the surfing community for its gnarly winter storm swells—in fact, newbies are often surprised at just how many shops and instructors there are everywhere from Newburyport up to Portland, Maine. For those just getting their feet wet, though, summer and fall in York Beach—with its sandy shores and gentle waves—is the perfect time to learn. Start the day with a latte at Central Bean & Bakery, where you’re likely to encounter other surfers fueling up before paddling out. Once you’re ready to try your luck hanging 10, the experts at Liquid Dreams Surf Shop will get you started on the right course, whether that’s hooking you up with rentals, setting up a lesson, or helping you select your first board and wetsuit for purchase.

The area has been beloved by water-sports enthusiasts and families for decades, but it’s about to get a whole lot cooler thanks to the mod rooms and surfer vibes of the brand-new York Beach Surf Club, a completely fresh take on what was once a dusty motel. The new owners redid the space in what they call “Scandi-Maine” design, but the heart and soul of the property is a heated saline pool complete with food and beverage service right to your lounger. After spending the day paddling the waves—or even providing moral support from the comfort of terra firma—it’s definitely the place to be. —T.P.

Photo by Andrew Burr

3 More Daring Getaways

1 Rock Climbing New Paltz, New York

Drive Time from Boston 3 hours, 30 minutes

Known as one of the best climbing spots in the U.S., Shawangunk Ridge (affectionately called “The Gunks”) is an enormous bedrock ridge that stretches from New Jersey to just north of the town of New Paltz in Ulster County, New York. Whether you’re a beginner looking for a rock-climbing 101 course or a seasoned pro in need of a guide to brush up on your skills, the experienced instructors at Eastern Mountain Sports Schools offer a range of courses as well as private and family group lessons. When it’s time for a little R&R after a full day of climbing, check into the tony Mohonk Mountain House, where the award-winning spa is well versed in tailoring treatments to tired arms and legs. —T.P.

Photo courtesy of Preserve Sporting Club

2 Hunting and Clay Shooting Richmond, Rhode Island

Drive Time from Boston 1 hour, 30 minutes

Close your eyes and picture a place with 3,500 unspoiled acres teeming with pheasants and wild turkeys. No, we’re not talking about the northern woods of New Hampshire or Maine; we’re talking about the Preserve, a Rhode Island hotel, residential development, and sporting club that offers a bucolic escape from the demands of city life just 80 miles from Boston. Get comfortable inside one of the luxurious cabins, suites, or multi-bedroom homes available for rent—or check out the new safari-style glamping tent and cigar experience on offer this fall—then let the property’s guides set you up for clay shooting, continental hunting, or even a pheasant tower shoot.  —T.P.

Photo by Greg Hartford

3 Exploring Mount Desert Island, Maine

The Pine Tree State is about more than just lobsters and wild-blueberry everything. With the highest coastal mountains on the Eastern Seaboard, there are enough trails in Acadia National Park to entice any adventurer—don’t miss hiking or driving Cadillac Mountain at sunrise (pictured)—not to mention plenty of gentle carriage roads for less-daring explorers. And while outdoor excursions always take center stage this time of year, the area still has plenty of creature comforts, whether you prefer staying in a West Elm–furnished glamping tent at the brand-new Under Canvas, or at the recently renovated Claremont Hotel, where the waterfront Batson Fish Camp restaurant offers panoramic views over one of the only fjords in North America. —T.P.

Thrills by the shore in Seaside Heights. / Photo by Americana/Alamy Stock Photo

The Jersey Shore

Drive Time from Boston 5 hours

Forget the fist-pumping crowds of beer-slinging, sun-worshiping twentysomethings you’ve seen on TV. Though in recent years this stretch of coastline has gotten the reputation as a party spot thanks to a certain MTV show, the area is actually an ideal place for kids, with plenty of boardwalks featuring carnival-style rides and amusements and all the old-fashioned shore fun (think: taffy, fudge, and soft-serve custard) that families here have been enjoying for generations, plus a few new surprises along the way.

Kid-friendly fun at the Jersey Shore. / Photo by Danita Delimont/Alamy Stock Photo

The region is also a lot bigger than you might think, stretching from the New York border all the way south to Cape May, and each town has its own unique vibe. On the southern end, the Wildwoods’ 38-block boardwalk offers more than 100 rides spread out over three piers, not to mention two water parks steps from the sand. Of course, there’s plenty for the adults to love, too, including the recently renovated Shore House in North Wildwood, built on the foundation of a classic 1960s motel but beautifully updated for the 21st century. Nearby Ocean City also boasts rides, go-carts, and all the pizza and fries you can eat on its bustling boards. Mornings, meanwhile, are for pedaling a four-wheeled surrey as the salt air whips your hair.

Though you won’t find a ride-heavy boardwalk in revitalized Asbury Park, farther north, you will find the Asbury Splash Park, mini golf, and the Silverball Arcade just off the beach—plus a recently opened boutique hotel, the Asbury Ocean Club, with a stunning pool overlooking the water. If the kids are still begging to hop on a Ferris wheel, Casino Pier in Seaside Heights—yes, the one made famous by Snooki and JWoww—is only a 45-minute drive, and packed with enough thrills, including the brand-new Xolo Loca roller coaster, for a whole day of fun in the sun. —Brittany Jasnoff

Jumping in on the Vineyard. / Photo by Elizabeth Cecil

Photo courtesy of Winnetu Oceanside Resort

2 More Kids’ Getaways

1 Winnetu Oceanside Resort Martha’s Vineyard

Travel Time from Boston 2 hours, 30 minutes

Owners Mark and Gwenn Snider believe that everyone should feel like a kid on vacation—which probably explains why their plush resort, just a short stroll from South Beach in Katama—has everything under the sun that families need to let loose and relax, quite literally. A complimentary day program for children featuring treasure hunts, art projects, and nearby field trips through early September? You got it. An on-site babysitter at the Dunes restaurant, so parents can unwind al fresco with a cocktail at sunset? Of course. Lemonade, cookies, and antique fire-truck or jitney rides every day starting at 2 p.m. for all ages? Sign us up. —B.J.

Photo courtesy of Legoland New York Resort

2 Legoland Goshen, New York

Any adult who has stepped on a piece of Lego in bare feet can attest to children’s abiding love for this classic toy. Now, the whole clan can experience its infinite wonders at the massive Legoland Resort that opened this summer in upstate New York. The $500 million theme park took five years to build and features rides and attractions based on the brand’s most popular toys. The Legoland Hotel has themed rooms ranging from pirates to ninjas, and beyond rides like the Dragon’s Apprentice mini coaster and DJ’s Dizzy Disco Spin, the interactive complex lets kids feel like they’re actually a part of the action. Shoes most definitely recommended. —Jonathan Soroff

A tempting spread from La Perche. / Photo by Nishat Khan/ @nishatnguyen

Drive Time from Boston 3 hours

During the pandemic, hordes of die-hard New Yorkers fled their fair city—but on the bright side, that means a food and drink revolution has flourished in the Hudson Valley, a place with the history and charm of New England but a distinct flavor all its own. It’s entirely possible to spend several days—or weeks, in fact—zigzagging through the region, but a single weekend in the town of Hudson is a great introduction to what you’ll find in the area: farm stands spilling over with seasonal produce and homemade baked goods; every sort of restaurant, from farm-to-table favorites to high-brow fine dining; and an abundance of craft breweries.

Make the exquisitely hip Maker Hotel your home base as you make your rounds through the town’s greatest hits, from pork-belly bao at Hudson Food Studio, to Wm. Farmer and Sons’ mouthwatering cast-iron foie gras with pistachio butter and rhubarb jam, to the cod cheeks with spring vegetables at Le Perche. Of course, it wouldn’t be a visit to Hudson without sampling the award-winning Tainted Senorita coffee stout at Hudson Brewing Co., the best place in town to ply locals for their favorite places to eat and drink. When you’re ready to turn in for the evening, head back to the hotel—but not before stopping by the Lounge for a nightcap. After all, it’s hard to think of a more quintessentially Hudson experience than a round of bourbon smashes inside the restored 19th-century carriage house. —T.P.

Photo courtesy of Bellini

2 More Gourmet Getaways

1 Providence Rhode Island

Drive Time from Boston 1 hour

As if Providence didn’t offer enough mouthwatering reasons for an Italy-inspired culinary road trip—hot spots Enoteca Umberto and Pane e Vino among our favorites—the new Beatrice hotel, a boutique property that’s set to open in September, boasts the first outpost of the Cipriani restaurant empire in New England. The hotel is named after developer and former mayor Joseph Paolino’s mother, and the sleek wood, white, and gray rooftop restaurant, Bellini (pictured above), pays homage to the cocktail invented at the Cipriani family’s most iconic property, Harry’s Bar in Venice. Like the rest of the Cipriani eateries, this one will feature regional specialties, making it a quick trip to Italy, senza passport. —J.S.

Photo by Matthew Perrin/Beba

2 Montreal Quebec, Canada*

When you can’t spare the time or expense for a proper European escape, a weekend in this Canadian gastronomic capital is a more-than-worthy replacement. Thanks to its diverse population, Montreal is in the midst of a culinary revolution, making eating your way through the city more exciting than ever. Start by booking a room at the Hotel William Gray, Old Montreal’s most adorable boutique hotel. From there the sky’s the limit: Try the Argentinian-Mediterranean fusion at Beba (pictured below); Ethiopian at East Africa Restaurant; grilled Portuguese fare at Ma Poule Mouillée; classic French bistro dishes at L’Express; and, of course, poutine at the kitschy Gibeau Orange Julep. Walk it off with a stroll through the cobblestone streets of Old Montreal and listen to passerby speaking French for an experience that’s nothing short of transporting. —T.P.

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Page not found – Boston Magazine

Oral history: the 1999 all-star baseball game that saved fenway, so, you want to live in chatham, our guide to the 12 best restaurants on nantucket, the 13 best restaurants on martha’s vineyard right now, in this section.

18 Wonderful Weekend Getaways from Boston

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Sometimes you just need a little mini-vacation to reset, and weekend getaways from Boston are perfect for that! If you’re looking to plan the perfect adventure away from Boston , then check out this list of easy weekend trips from Boston that will have you returning to the city recharged and ready to jump back into the grind! 

Best of all, with the driveability of New England , you can take a quick New England roadtrip and head to destinations all around the region for your weekend escape.

Table of Contents

Weekend Getaways from Boston

Make a beeline for the berkshires.

This one is a no-brainer, right? If you’re looking to get away from The City on a Hill for a little weekend reset, you don’t even need to leave the state because the Berkshires can offer both fun and relaxation! If you’re looking for a weekend getaway in the fall, there are multiple choices for prime leaf-peeping and apple-picking , and if you’re looking for a little more adventure, there are several options for that too, including some of the coolest hikes in New England!

If it’s more of a romantic getaway you’re after, consider renting a cozy Berkshires cabin during your weekend trip from Boston. Whether you’re into action, respite, or romance, the Berkshires is an ideal weekend getaway from Boston.

If you’re looking for a modern, romantic place to stay, book a room at 33 Main!

Click Here to Check Prices & Book!

Check in and check out for the weekend in Old Saybrook

Saybrook Point Resort and Marina in Old Saybrook, CT means a weekend getaway of rest and relaxation on the lovely Long Island Sound with amenities and accommodations to die for. Room options include stellar views over the Long Island Sound, fireplaces, and private balconies.

If you are planning a romantic weekend getaway from Boston, the Lighthouse Suite was voted the “Most Romantic Place to Stay” by Connecticut Magazine and features 360-degree views of the coastal oasis of Old Saybrook, CT, so hint, hint on that…

No matter where you stay, Old Saybrook is definitely one of the best beach towns in New England to visit.

Spend the weekend sampling all Portland has to offer

Portland, ME is well-known as a foodie destination, and is an interesting and eclectic mix of trendy hipster vibes and historical sophistication; you can find breweries , museums, lighthouses , shopping, coffee shops, bakeries , sailing, and cruises in Casco Bay, nearby hiking trails , and so much more . In fact, you can find a ready-made itinerary of all the must-do, must-see, must-eat & drink spots to visit for a perfect weekend getaway in Portland here , including recommendations for the best hotels and Airbnbs in Portland.

Portland Harbor Hotel has a very cool vibe.

Stay in stunning Stowe

A must-add to any weekend getaway list , the gorgeous ski town of Stowe, VT is perfect for a weekend trip from Boston! Travel + Leisure named Stowe as one of America’s Best Ski Towns , and Stowe has a lot more to offer beyond just their spectacular ski slopes.

There are many things to do in Stowe, including hiking and checking out the top restaurants , breweries, and breakfast places and if you’re looking for a spot to rev up the romance, well, Stowe also made it on this list of romantic getaways in Vermont, too!

This is one of my favorite New England day trips , period.

There are lots of cool Stowe hotel and Airbnb options to pick from, but a stay at the Trapp Family Lodge is quintessential Stowe!

Venture into North Conway

If you are looking for a weekend getaway from Boston to enjoy a variety of adventurous outdoor activities, then North Conway might just be the perfect destination for you! In the winter, you can hop on a snowmobile as the snow falls softly all around you, and in the summer, you can kayak or tube down the river as the sun glistens off the water with highly-rated Northern Extremes .

There are plenty of fun things to do here, but don’t forget to check out one of the region’s favorite outlet malls, Settlers Green , where you can shop at all 60+ retailers TAX-FREE! There are lots of solid options for where to stay and where to eat in North Conway, too, and North Conway Grand Hotel is a cool place to stay.

Indulge in some Gilded Age glory in Newport

Newport, RI is one of the most beautiful cities on the New England coast, and one of the top weekend getaways from Bostson sure to make anyone feel like they have stepped into another world far, far away from the hustle and bustle of the city.

Newport is well-known for its beautifully preserved Gilded Age era mansions, gorgeous beaches, delicious restaurants, and the scenic Cliff Walk , and it’s hard not to get swept away in the romance of this enchanting city, so if you are looking for a romantic getaway , check out these cool hotels and Airbnbs in Newport , too. If you’re looking to splurge, check out Castle Hill Inn!

Retreat to Rockport

Just about an hour up the road, lovely Rockport, MA makes for a great quick weekend getaway from Boston! You’ll love the stunning natural scenery of Cape Ann and the man-made charm that includes the row of rainbow houses and Motif #1, the bright red fishing shack that attracts artists from all around the world to capture its essence.

Whether you spend your weekend in Rockport checking out the local art on Bearskin Neck or lounging on the beach, this picturesque seaside village offers plenty of options for anything a person might need to relax and unwind for the weekend, including interesting inns, amazing restaurants, and some of the best breakfast options on Cape Ann! Plus, with Rockport being such a short trip from Boston, it can be the perfect overnight trip spot.

Check out our review of Emerson Inn ; definitely a cool place to stay in Rockport!

Go for a wild weekend in Acadia National Park

Okay, so spending the weekend visiting Acadia National Park doesn’t necessarily mean you will be going “wild,” but it’s the perfect place to enjoy the wild beauty of coastal Maine. It is just under 5 hours drive to get to Acadia from Boston, so this one is probably best reserved for a long weekend from Boston trip.

Whether you stay in one of these beautiful Airbnb s, charming inns , cute cabins , or you decide to rough it by camping on your own, there are so many ways to enjoy the stunning scenery of Acadia National Park. Hiking is a given, but leave the plan loose with plenty of time to explore other activities too (like whale watching!) and you can even use this thoughtfully planned 3 Day Itinerary to guide you.

Consider booking a room at Bar Harbor Manor for its convenient downtown location!

Lose your stress in Litchfield Hills

When you are looking for a laid-back weekend getaway from Boston to escape the stress and pressure of big city life, look no further than the region of Litchfield Hills, CT. known for its scenic backdrop that includes picturesque covered bridges and rushing waterfalls.

In fact, this area is such a perfect example of New England charm that the village of Kent was included in our list of Charming New England Towns to Visit in the Fall . When it is laid-back and restful vibes you are after on your weekend getaway from Boston, consider booking  a room at lovely Litchfield Inn for lovely scenery and fantastic service.

Pop in to Providence for a weekend well-spent

Providence is its own unique brand of hip, and because it takes less than an hour to travel to, it make the perfect weekend trip from Boston spot. There are museums, funky outdoor flea markets, cool, historical landmarks, and Water f ire , an internationally known annual art installation event that draws people in from all around the world.

There are so many great things to do in Providence , including breweries, coffee shops, restaurants, breakfast spots , hotels, and more; consider a stay at historic Hotel Providence in downtown PVD!

Pack your bags for Portsmouth

Portsmouth is just a quick drive up from Boston, but this weekend getaway destination will still take you worlds away from all the hustle and bustle of the city! This cute coastal New Hampshire town offers a ton of museums and historical monuments , incredible food options , cool breweries , breakfast places , and more. There are plenty of options for where to stay in Portsmouth including some pretty awesome Airbnb stays, too.

Any time of year, Portsmouth is the perfect Seacoast weekend getaway from Boston; consider booking a room at The Hotel Portsmouth for its excellent amenities and location.

Have the best time in Burlington

Burlington is the perfect spot for a Vermont weekend getaway from Boston! This hip and artsy college town has a lot to offer visitors, like some extra cozy coffee shops , unique breweries and bars , excellent restaurants , great breakfast spots , and some fantastic hiking. There are plenty of cool options for where to stay in Burlington , including awesome Airbnbs , and if you are traveling with your pup, Burlington is extra pup-friendly with lots of restaurants, hotels, and activities that welcome you and your pooch, too!

Consider a stay at Hilton Garden Inn Burlington Downtown to be just 2 blocks from Burlington’s famous Church Street!

Lap up luxury in Nantucket

For the ultimate luxury weekend getaway from Boston, look no further than The Wauwinet in Nantucket, MA! Adults only, this stunning seaside resort is the only Relais & Chateaux hotel on the island and when you are there, you will feel like royalty.

There are so many great things to do in Nantucket, from the beaches to the restaurants and beyond, but if it’s a romantic trip from Boston you’re planning, The Wauwinet is one of the most romantic hotels in the US and you will see why from the moment you check in.

Explore the magic of Mystic

The waterfront village of Mystic is less than a 2 hour drive from Boston, making it an ideal weekend vacation near Boston, and not just because you can visit the actual Mystic Pizza that the Julia Roberts movie was based on!

Located on the Mystic River, Mystic offers all kinds of fun ; visit the Mystic Aquarium, sample some local flavors , and consider a stay at one of the top Mystic hotels, like The Whaler’s Inn.

Visit the history, mystery, and intrigue of Salem

Salem remains a hotspot for all intrigued by its infamous past, but there’s more to explore here than just historical drama on its hallowed streets. Of course, there are a lot of activities around Halloween , including ghost tours and checking out all the locations that Hocus Pocus filmed in town , but all year round you can find interesting museums, novelty shops, reputedly haunted places , and psychic encounters that will let you get a bit of a taste of the occult yourself. Salem’s motto is “Still making history,” and when you spend your weekend getaway sampling the tastiest restaurants and staying in the coolest Airbnbs and inns , you’ll see how that’s true!

Want to stay at one of the most haunted hotels in New England ? Consider booking a room at Hawthorne Hotel!

Make memories in Manchester, VT

Nestled in the Green Mountains, Manchester is one of those picturesque towns in Vermont and offers something for every kind of visitor .

There’s great hiking, a cute downtown, historical Hildene, the Lincoln Family Home , and more to keep you busy, and w ith fabulous restaurants and lodging options , Manchester is a great choice for a weekend getaway from Boston that will leave you feeling refreshed and ready to go on Monday.

Check out Kimpton Taconic Hotel for rustic charm within easy walking distance of all kinds of fun downtown Manchester things to do.

Be cool in Cape Cod

A Cape Cod vacation from Boston is nothing short of paradise any time of the year, and just a quick hour drive to get there. P lanning your weekend getaway from Boston for warmer weather means you can enjoy the beaches a little more, but Cape Cod in the fall is its own lovely experience, too.

Cape Cod has great dining, hotels , and Airbnb options , wineries to visit, lobster rolls to sample, hikes to take , and more, and the biggest issue you will find on your weekend getaway from Boston will be narrowing down your choices; which Cape Cod towns will you visit? Provincetown ? Wellfleet ? Chatham ? Be sure to scope out some of the best things to do in Cape Cod with kids if you’re planning a family trip from Boston!

We recently stayed at Captain’s House Inn in Chatham and loved it! Check out our experience here .

Click Here to Check Prices & Book !

Slow down on Block Island

Block Island has just about every ingredient to make the perfect summer weekend getaway: beaches, bluffs, lighthouses, and all the amenities you could possibly want. Beautiful Block Island has plenty of options for where to stay , fun things to do , and great restaurants to eat at. Block Island is the perfect spot for a summer weekend trip from Boston!

Consider a stay at Old Town Inn while on Block Island for excellent service, coastal modern rooms, a phenomenal breakfast, and fantastic location for beaches, a lighthouse, and more.

Weekend getaways are always an excellent option for decompressing and letting off a little steam. You work hard all week, hope this list helps you choose the best weekend getaway from Boston for you!

You might also like:

• 50 Things to Do in Massachusetts: Your MA Travel Guide
• 15 Great Places to Babymoon in New England
• 7 Fantastic Weekend Getaways in Connecticut
• 7 Weekend Getaways in Massachusetts for Bay State Fun!
• 18 New England Weekend Getaways from NYC

Watch CBS News

Hurricane Beryl snarls travel in U.S. as airlines cancel hundreds of flights

By Aimee Picchi , Megan Cerullo

Edited By Alain Sherter

Updated on: July 8, 2024 / 4:32 PM EDT / CBS News

Hundreds of flights have been canceled Monday as airlines grapple with the impact of Hurricane Beryl making  landfall in Texas . 

Another roughly 3,500 flights were delayed, although not all delays are related to the hurricane,  according to flight tracking website FlightAware. Many of the disrupted flights are those originating in or flying to Texas airports, including almost 600 cancellations for departing flights at Houston's George Bush Intercontinental Airport (IAH) and 165 outbound flights at William P. Hobby Airport, also in Houston.

United Airlines had the greatest number of canceled flights on Monday morning, with 486 cancellations, followed by Southwest with 346, FlightAware's data shows.

Beryl made landfall as a Category 1 storm, with sustained winds of 74 to 95 miles per hour, although on Monday it weakened to a  tropical storm  with maximum wind speeds near 70 mph. Even a less powerful hurricane carries risks of flooding and storm surge, and rainfall in the Houston metropolitan area has reached between 2 to 3 inches per hour, with the region potentially facing up to 12 inches of rain as well as flash flooding, CBS News senior weather and climate producer David Parkinson said.

Beryl, the second named storm in what is predicted to be a busy hurricane season in the Atlantic, which runs from June 1 to Nov. 30, is expected to  move  over eastern Texas Monday, then pass through the Lower Mississippi Valley into the Ohio Valley on Tuesday and Wednesday, according to the National Hurricane Center.

In a statement to CBS News, United said it is largely suspending flights out of Houston on Monday, but will waive change fees and fare differences for passengers who want to reschedule their trips. United flights at IAH are suspended through at least 5 p.m. Eastern Time. "That will adjust based on conditions as the storm passes through," the airline said. 

Likewise, American Airlines told CBS News that it is suspending operations at Houston airports on Monday until about 3 p.m. Eastern Time.

"We'll evaluate conditions tomorrow to determine if it's safe to resume operations in the afternoon/evening," American said in a statement, adding that customers can also rebook their tickets without change fees. The carrier said it doesn't plan to change its Texas flight schedules in Austin, Brownsville, Harlingen or McAllen due to the storm. 

Southwest Airlines said in a statement that it has canceled flights at George Bush Intercontinental Airport, William P. Hobby Airport and Corpus Christi International Airport through noon on Monday.  The carrier added that it expects schedule changes through Monday afternoon and urged customers to check their flight status for any disruptions.

—With reporting by CBS News' Kris Van Cleave.

• Hurricane Beryl

Aimee Picchi is the associate managing editor for CBS MoneyWatch, where she covers business and personal finance. She previously worked at Bloomberg News and has written for national news outlets including USA Today and Consumer Reports.

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Travel surges in New England over July 4 weekend as US air travel breaks records

Agents for the us transportation security administration on sunday screened 3 million airline passengers in a single day for the first time ever.

Airline passengers traveled like never before this Fourth of July weekend — many of them bound for the spiritual birthplace of America in New England.

More than 3 million people passed through US airport security on Sunday, the first time that number of passengers have been screened in a single day, according to the US Transportation Security Administration. Of those, 76,323 passengers — roughly 2.5 percent of the national total — passed through Logan International Airport.

Though Sunday was only the seventh-busiest day of the year so far for Logan, it was just a few thousand travelers short of breaking this year’s record of 79,581; that number was set on April 12 (the Friday before Patriots’ Day Weekend).

Part of the increase at Logan may be attributed to the new 320,000-square-foot expansion to Logan’s Terminal E. The striking “Boston Red” structure opened to the public last August, adding four extra gates (and space for more) serving international destinations.

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Other regional airports saw high numbers as well, including Bradley International Airport in Connecticut, which processed 11,418 people on Sunday — also nearly breaking their record of 12,578 set on April 11 — and Providence’s T.F. Green International Airport, which screened a record 8,260 travelers.

On the other hand, Manchester-Boston Regional Airport saw just over 2,000 passengers screened. Manchester’s passenger high-water mark for passenger screenings (2,914) was set on June 24, though it has not yet exceeded last year’s high of 3,085, set on April 20, 2023.

The national record, which was widely predicted to happen at some point over the Fourth of July holiday weekend, topped the June 23 mark of more than 2.99 million screened passengers.

Eight of the 10 busiest days in TSA’s history have come this year as the number of travelers tops pre-pandemic levels.

That’s certainly true at Boston Logan, where passenger travel continues its healthy rebound from 2020. In May, the airport saw over 3.9 million travelers pass through its gates, an increase of approximately 6 percent from the previous year, according to Massport data.

While Americans continue to grapple with inflation, travel costs including airline tickets and hotel prices have eased significantly from a year ago. Hotel rooms were 1.2% cheaper in May compared with a year ago, according to recent government inflation data. Those costs have been trending lower since the beginning of the year.

While most US airlines lost money in the first quarter — traditionally the weakest time of year for travel — they were all expecting a summer of full planes.

This spring, American and Southwest said they expected solid second quarter profits. They joined Delta Air Lines and United Airlines in giving an upbeat outlook for the April-through-June period, which includes the start of peak season for carriers.

Delta reports its second-quarter earnings on Thursday, with analysts predicting sales of $15.5 billion, nearly $1 billion more than the same period a year ago. Next week, United and American issue their quarterly results, with Wall Street forecasting higher revenue from a year ago for both carriers.

Material from the Associated Press and previous Globe coverage was used in this report.

Camilo Fonseca can be reached at [email protected] . Follow him on Twitter @fonseca_esq and Instagram @camilo_fonseca.reports .