Plan A Perfect Boston Weekend Trip

Boston, Massachusetts, is one of our favorite cities to visit in the United States. It was our first trip together when we were dating. It is also the place where we got engaged. We have been back many times since then and will continue to revisit throughout our lifetime. It was in the running for our long-time home for a while. I still dream about retiring to a beach house on Cape Cod, but I’m happy to enjoy Boston weekend trips for now. 

Bean Town is easy to navigate on public transportation, so it’s a great place to fly in and spend a few days exploring. You’ll feel like you’ve been transported back in time with so much history and cool architecture throughout the streets of this harbor city. We broke down our favorites by neighborhood to help you plan the perfect Boston weekend getaway.

All the Basics for a Weekend in Boston

Getting around Boston

Boston has great public transportation. The “T” will get you all over town, and you can get a 7-day pass for $22.50, which is a great deal if you are visiting for a few days. This city is also very walkable, with lots to see in every neighborhood. The subway is similar to New York City, just on a smaller scale. For a quick Boston weekend trip, avoid car rentals.

Where to Stay in Boston

The CitizenM Boston is right downtown. We love this hotel chain. There are beautiful common spaces and well-equipped rooms. If you need a lot of space, this would not be your jam. But if you plan to spend more of your time outside exploring, this is a great option. I usually just require a comfortable bed and a clean bathroom—this hotel is that, but with an elevated style.

If you want to stay near the water and be close to some of the popular attractions near the harbor, book your stay at the Envoy Hotel. We haven’t personally stayed here, but it’s on our list for our next trip because it looks gorgeous and has great reviews.

The Verb Hotel and Hotel Commonwealth are the best locations if you want to stay near Fenway Park. It’s still easy to get around on the train, so you can stay in a neighborhood instead of downtown.

If your heart is set on the back Bay Area, I recommend the Charlesmark Hotel. It’s a smaller boutique hotel, but very comfortable. It looks right out over the finish line for the Boston Marathon. We’ve stayed here a few times and loved the location.

Cambridge is also very accessible to all the major tourist sites but has a totally different vibe than downtown Boston. The Kimpton Marlowe is a beautiful property, and we are always huge fans of Kimptons because they are so dog friendly. Read below for more info on things to do in Cambridge.

Our Favorite Introduction to Boston – The Duck Tour

If you have never been to Boston before, the Boston Duck Tour is the best way to get a full introduction to the city. This tour goes over land and through the water, exploring some of the top sites in the city. The guides mix silly dad jokes with fascinating stories about the city’s history. I’ll admit that we’ve taken the same tour on three different trips because we’ve had other people with us that had never done it, and I cannot recommend it enough. 

Things to Do on a Boston Weekend by Neighborhood

Maximize your Boston weekend adventure by planning your activities based on location so you aren’t bouncing all over town. See which of these neighborhoods sounds most appealing to you and plan to stay there and then venture out to see more during the day. 

Downtown

Many of the most popular tourist attractions are in the city center. You could spend your entire Boston weekend trip here and still not see everything. The city was founded in 1630 and started here in the downtown area. It’s home to the financial district and most of the important government buildings. It’s easy to get around the city center by public transportation or walking. 

Quincy Market & Faneuil Hall

This is a great place to visit when you’re hungry. There are so many different food vendors and great shopping spots. Get in line at Boston Chowda or The Nada Cart for a quick bite. Find fresh seafood, incredible desserts, and savory warm dishes for cold, rainy days. It’s a great place to grab lunch, especially if you are traveling with a group with various tastes. You’ll see a few chains, like Dick’s Last Resort and McCormick & Schmicks, but even those are fantastic restaurant options. 

These two buildings have a ton of history and have been staples in the downtown area for almost two hundred years. It’s been a shopping destination and used to be the main place to get groceries and other necessities. Today, you’ll still see some produce and grocery goods, but most shopping stalls are souvenirs and unique gifts. 

North End

This part of Boston has so much history. The North End is the city’s oldest residential community and has been inhabited since 1630. Visit the Old North Church and see the home that Paul Revere actually lived in. Plus, you can eat some of the best Italian food in the whole Northeast region of the country. The 0.36 square mile area is home to dozens of incredible restaurants serving giant plates of pasta and other Italian specialties. Save a little room for desserts at Modern Pastry. Also, see if you can find the narrowest house in Boston. 

Freedom Trail

If you are visiting the North End, you will find the Freedom Trail walks right through that neighborhood. This free, easy walkway through the city highlights many important places in our country’s history. The full trail is 2.5 miles with 16 different stops, making it a perfect activity for a day of historical sightseeing. Get the full explanation of stops along the route using the free online brochure. 

Boston Public Market 

The Boston Public Market is my other favorite place to eat so much food. Tons of stands serve up amazing local treats. The market opened less than 10 years ago and exclusively features New England vendors. You’ll find seafood, meat, eggs, produce, baked goods, specialty items, and crafts. Plus, there are tons of prepared meals to order and eat on the greenspace outside or at the community spaces at the indoor market. We’ve tried fresh pressed juices, coffees, and baked goods here, and the vendor list is constantly changing. 

Union Street

A section of Union Street bars and restaurants has been around longer than most Beantown spots. The Union Oyster House is a famous establishment, and it’s a great spot to grab a bite to eat, especially if you like seafood. The Bell in Hand Tavern is another historic spot for grabbing drinks and people-watching. While you are in the area, make sure to walk through the New England Holocaust Memorial in the park across the street. 

Rose Kennedy Greenway

The Greenway is 1.5 miles of beautiful green space in Boston’s downtown area. There are fountains, food trucks, public art displays, beer and wine gardens, and beautifully landscaped areas. It runs from the North End around downtown and towards Chinatown. Rent a bike and cruise the stretch on two wheels or just explore a section of the park when you need a break. 

Harbor Cruise and Waterfront

The Boston Harbor is a major shipping center in the northeast. It’s home to the famous Boston Tea Party, but the history goes back even further. Get out on the water by taking a harbor cruise or enjoy a rooftop patio along the waterfront. There are more than 30 harbor islands, plus tons of wildlife living in the harbor area that can be spotted from a harbor cruise. Whale-watching tours are also available during certain seasons. 

Beacon Hill

Beacon Hill is adjacent to downtown and might even be considered part of the city center, but it’s my favorite part of the city and so I wanted to highlight it separately. The hill is home to the Massachusetts States House and some of the most beautiful historic rowhouses in the city. Plus, the brick sidewalks and gaslit lanterns make you feel like you’ve traveled back in time. In my opinion, you should not miss exploring this neighborhood.

Historic District of Beacon Hill

A simple walk together through one of Boston’s most beautiful and historic neighborhoods, Beacon Hill, is one of my favorite things to do in the city. These cobblestone streets have been home to politicians, poets, and celebrities for years. While the streets can sometimes get busy with tourists, the mornings are usually quiet and perfect for fresh air. Grab a coffee at Blank Street Coffee and then spend an hour or so winding through the different blocks, appreciating each home and picking out your favorite. Sign up for a free self-guided walking tour and dive deeper into the history.

Boston Common

The Boston Common is the oldest city park in the United States. It’s a beautiful place for a walk. Check out the Frog Pond (which is a skating rink in the winter) and the many historic monuments placed along the walkways. You’ll enjoy beautiful views of the Massachusetts State House on the northern edge. You can also visit the Boston Public Garden just across Charles Street. 

The Original “Cheers” Bar

The TV show Cheers was incredibly popular during its run and you can visit the bar that served as the inspiration and even some of the background shots. It was originally called Bull and Finch, but it has been renamed in recent years and embraces its television fame. While we were not really the generation that watched the show, we definitely know the theme song and loved that you can order Sam Adams Brick Red on tap here (it’s uncommon to find.)

Back Bay

The Back Bay neighborhood was built up when the need for more luxury residential housing came up in the 1800s. You can still see the beautiful Victorian homes among the large commercial skyscrapers that were added to the neighborhood in the last few decades. The neighborhood is known for shopping, hotels, and the tallest building in the Boston skyline, the John Hancock Tower.

Newbury Street

Top fashion brands have storefronts along the swanky Newbury Street. There are great local shops and specialty shops as well. Even if you aren’t a big shopper, this is a great stretch of restaurants and cool architecture. Enjoy some window shopping or a sidewalk cocktail where you can do some people watching if that’s more your vibe. 

Boston Public Library and Copley Square

Copley Square is home to the finish line of the Boston Marathon and the large Boston Public Library. Visit the lively farmer’s market that sets up here weekly or just sit and enjoy the sunshine and people watching in this busy neighborhood. Explore the Trinity Church or Old South Church or head to the Sky Observatory at the top of the John Hancock Tower. 

Make Your Own Food Tour

Boston’s Back Bay is home to some of the best restaurants in the city. It’s a great place to visit when you’re hungry. You can find a variety of flavors. Here are some of the top-rated spots that are worth checking out, but you won’t go wrong just walking and following your nose.

• Vegan ramen at Red White
• Lady M Crepe Cakes
• Fried Chicken & Waffles at Buttermilk and Bourbon
• Greek food at Krasi

Charles River Esplanade

The Charles River Esplanade is a 17-mile stretch that is state-owned and runs along the Charles River. One of the most popular sections is right in the Back Bay. You can head to the river and use the well-maintained paths to walk along the water. The Boston Pops hold their summer concerts at the Hatch Shell on the Esplanade as well.

Fenway-Kenmore

Sometimes recognized as two separate neighborhoods, the Fenway and Kenmore neighborhoods are adjacent to the Back Bay and home to some of Boston’s most popular attractions and college campuses. It’s easy to reach on the subway, so it’s a great place to stay if you want to be outside of downtown. If you are enjoying a summer Boston weekend, baseball might just have to be on your itinerary.

Fenway Park

Fenway Park is known as America’s Most Beloved Ballpark (unless you’re a Yankees fan.) It was built in 1912 and then updated in 1934, and even today, it retains most of the quirks and historical features of the original park. It’s hosted 11 World Series and been the backdrop of Hollywood movies (like Fever Pitch). Even if you aren’t a baseball fan, it’s impossible to ignore the energy and incredible history of this iconic building.

Daily tours are offered of the park and it was one of our favorite activities in Boston. Sit on the famous Green Monster, hear the stories of the legends who have played here, and see parts of the ballpark that the public doesn’t normally see. If the Red Sox schedule works out, grab tickets to a game too. You’ll find yourself singing Dirty Water for weeks afterwards because it is so much fun to be part of this crowd. 

Museum of Fine Arts

The Boston Museum of Fine Arts is the 20th largest art museum in the world with more than 450,000 works of art. The location was originally in Copley Square, but moved to the Fenway location in 1909 because it was obvious that they would need more space. Check out Egyptian artifacts, French impressionist paintings, Buddhist sculptures, and the largest collection of Japanese artworks under one roof outside of Japan. There are always traveling exhibits and collections on display as well.

Back Bay Fens

The Fens was once a spot of saltwater marshland that has been landscaped into a beautiful urban park. Check out the Kelleher Rose Garden and the Victory Garden that was planted by local citizens during World War II. You can also walk along paths and find statues and monuments dedicated to famous Bostonians, like baseball player and philanthropist Roberto Clemente.  

Cambridge/Somerville

These two cities are not part of Boston, but lay just across the Charles River and are incredibly accessible for people visiting Bean Town. Home to Harvard, MIT, and Tufts, you’ll experience all the fun energy of a college town while visiting, but there is plenty to do for those who aren’t looking to head back to school.

Harvard Square

Harvard University is one of the premiere Ivy League universities and has been operating in Cambridge since 1636. The campus is beautiful and worth a visit – set up a tour and learn more about the famous students and fascinating history. 

Harvard Square is the triangular pedestrian square that separates the business district with the campus and is home to an easily accessible subway station. You’ll find newsstands and coffee spots where you can grab a seat and watch students, tourists, and locals make their way to and from places. Street performers set up in the square often to provide a soundtrack.

Bow Market

Located in Somerville, this spot is great for foodies who want to try a variety of local flavors. With bakeries, breweries, pizzerias, and top-notch restaurants, there is something for every palate at the market. Food halls are a great way to experience a neighborhood. Bow Market also has a collection of retailers, so you can grab some locally designed clothes and decor, records or vintage goods. 

Inman Square

Inman Square is a lesser known Cambridge square that is accessible by several bus lines. The eastern Cambridge neighborhood is home to many students from MIT and Harvard and has a Brazilian and Portuguese influence. Try Muqueca, a Brazilian seafood restaurant where stews are made in traditional clay pots. Grab a bite at Trina’s Starlite Lounge, which features retro decor and great comfort food. Try fresh oysters at Puritan Oyster Bar. This is a great area to explore that is more off the beaten path.

Other Boston Weekend Attractions

Boston has so much to explore outside of the city center, but there is so much we have yet to explore and experience. There are two spots we wanted to highlight outside of the popular neighborhoods in Boston, but still easy to add to a Boston weekend trip.

Sam Adams Brewery in Jamaica Plain 

This brewery tour was better than we expected. They take you through a pretty quick brewery tour with some cool history and facts about beer. After the tour, you visit the tasting room, where you get to try 3 different beers – one of which will probably never hit shelves because it’s a rare test. The R&D beers were really interesting. I don’t think they still provide the party bus back to the subway station (which was my personal favorite), but it’s still a fun experience for beer lovers. 

John F Kennedy Presidential Library

It’s hard to visit Massachusetts and not do something Kennedy-specific. The museum at the JFK Presidential Library was fascinating. The permanent exhibits span his entire life, from childhood through his presidency. The first lady, Jackie Kennedy, has many exhibits and sections dedicated to her work throughout her time in Washington and for years after. The architecture is beautiful and it’s a great way for history buffs to spend an afternoon.

The Best Day Trips from Boston

A Boston weekend could be spent completely just experiencing the city streets, but it’s also conveniently located in the middle of some of the most beautiful coastlines of New England. Sneak away for a day trip to one of these favorite spots if you want to see more.

Provincetown

This town at the tip of Cape Cod is popular with artists, writers, and other creatives, and it’s a perfect escape from the hustle of the city. Take the fast ferry through the Boston Harbor and get dropped off right in the center of Main Street. Take the trolley tour that will show you some of the coolest historical homes in town, and take visitors to the National Seashore for views of the ocean and magnificent sand dunes.  

Climb to the top of the Pilgrim Monument and get 360-degree views of the cape. Take time to browse the unique galleries and shops along the Main Drag and enjoy a seafood lunch and some locally brewed beers before taking the ferry back to the city. You’ll catch the sunset with the skyline in the foreground if you’re lucky. This trip is our favorite because this is also where we got engaged. 

The Maine Coast and Portsmouth

The northeast is not a large area geographically, so getting around and exploring some of the other New England states on a quick day trip is pretty easy. Just a few hours north, you can explore Kennebunkport, Maine and the cool city of Portsmouth, New Hampshire. The Clam Shack is still one of my favorite food experiences of all time. I think about that fried clam sandwich all the time. See where the Bush compound sits on the oceanfront just outside of town. 

Portsmouth is a cool city to walk around and take in the history. Most people don’t even realize that New Hampshire has some waterfront. You’ll cruise through this port city to get to Maine, so it’s a great place to stop for an afternoon snack on your way back to Boston.

Salem

Halloween is the best time of year to visit Salem, Massachusetts, but if you are interested in the famous Witch Trials, you can tour and learn more any time of year. Take the walking tour and hear the stories of this haunted town. Visit the House of the Seven Gables and the many museums dedicated to the dark history of this beautiful New England town. Take the ferry from Boston if you want to avoid a car rental for the day. 

Final Thoughts on Boston Weekend

Boston is the perfect weekend getaway with a blend of history, incredible food, and all the unique pockets throughout town. It’s easy to get around town, and you can visit repeatedly and keep discovering new areas of town. It will always be a special place for us because it was the first place we traveled together and also where we got engaged a few years later. Plan your Boston weekend trip and hopefully, you’ll fall in love with this city too.

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