Top 20 Things to Do in Boston, Massachusetts

Boston Tea Party

TripSavvy / Violet Smirnova 

Boston is a one-of-a-kind American city that offers visitors opportunities to relive history, immerse themselves in the arts, cheer for hometown sports teams, explore museums, discover "hidden" harbor islands and imbibe at a famous brewery or an even more famous bar. If you're visiting Boston for the first time or if you've never spent an extended period in Massachusetts' capital city, here are our picks for Boston's 20 must-see places and attractions.

01 of 20

Walk Along the Freedom Trail

Freedom Trail in Boston

Violet Smirnova / TripSavvy

A walk along the two-and-a-half-mile Freedom Trail is one of the best ways to get acquainted with Boston and to efficiently visit the city's bounty of historic landmarks. If you're in a hurry and in pretty good shape, you can cover the length of the trail in as little as an hour, but that won't really allow you time to stop and visit any of the sites along the way. Your best bet is to allow three hours or more to walk the trail at a leisurely pace and see all of its Revolutionary landmarks. Boston also has an Irish Heritage Trail you may want to explore.

02 of 20

Visit the Boston Public Garden and the Swan Boats

People on a swan boat in Boston Public Garden

TripSavvy / Violet Smirnova 

Boston Public Garden, located along Charles Street adjacent to Boston Common, is the nation's oldest botanical garden. The famous Swan Boats have returned to Boston Public Garden each spring since they were first invented in 1877 by Robert Paget. The business, which operates from mid-April through Labor Day, is still run by descendants of the boats' inventor.

03 of 20

Shop (and Eat) at Quincy Market

Inside Quincy Market

 TripSavvy / Taylor Nealand 

Faneuil Hall Marketplace, the famous indoor-outdoor market, is a great place for both shopping and dining. Quincy Market colonnade houses more than thirty food merchants.

04 of 20

See a Reenactment of the Boston Tea Party

Boston Tea Party

TripSavvy / Violet Smirnova


The Boston Tea Party is reenacted daily, and you can participate. Really! Steep yourself in history at the Boston Tea Party Ships & Museum. Rebuilt and reimagined following a devastating 2001 fire and another in 2007, the attraction reopened in 2012, and it's now one of the city's most engaging experiences.

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05 of 20

Watch the Red Sox Play at Fenway Park

Wide shot of the exterior of Fenway Park

TripSavvy / Violet Smirnova 


On a sunshine-filled summer afternoon, there is perhaps no better place to be in all of New England than Fenway Park, the historic home of Major League Baseball's Boston Red Sox. Baseball fans have been energized and agonized by the exploits of some of baseball's greatest players at Fenway since 1912. If you can't score tickets to a Red Sox game, look into behind-the-scenes tours of Fenway Park.

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Visit the Museum of Science

Boston Museum of Sceince

TripSavvy / Violet Smirnova


Boston's museums are as good as any you'll find in the world, and one of the most visited is the Museum of Science at Science Park. It has more than 700 interactive exhibits including A Bird's World, a 4-D theater, Thrill Ride 360°, a butterfly garden and a planetarium. Take the kids!

07 of 20

Taste Beer at Sam Adams Brewery

Sam Adams Brewery SIgn

Violet Smirnov / TripSavvy

These days, Samuel Adams is known as much for being a brewer as a patriot. Tour the Sam Adams Brewery in the Jamaica Plain neighborhood of Boston for a glimpse of the beer-making process and a sample of the finished product. The brewery is also home to the Boston Beer Museum.

08 of 20

Visit the New England Aquarium

New England Aquarium Harbor Seal
Courtesy of the New England Aquarium

Want to see sea lions smile and penguins play? Head to the New England Aquarium, one of Boston's perpetually popular family attractions. Once inside, you'll find yourself immersed in a watery world, where you can wave your flippers at cavorting sea lions and press your nose right up against the glass of the poisonous fish tank—if you dare!

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09 of 20

Take a Day-Trip to a Boston Harbor Island

Boston Harbor Islands

Kim Knox Beckius

Want to swim, hike, explore the ruins of an old fort and camp out under the stars at a National Park? Believe it or not, you can do all of these things without leaving the city of Boston. The Boston Harbor Islands National Recreation Area consists of 34 narrow isles scattered in New England's most historic harbor, and you can visit these "hidden" outdoor spaces by boarding seasonal ferries from Quincy and Boston's Long Wharf.

10 of 20

Eat Your Way through Boston’s Chinatown

Gate in china town with sun poking through

TripSavvy / Violet Smirnova 

Chinatown is one of Boston’s most vibrant neighborhoods, an entry point for generations of immigrants and home to thousands of people. It is home to a diverse amount of eateries, grocery stores, noodle and dim sum restaurants, bubble tea cafés, and herbal shops, all along with the usual convenience stores and gift shops.

11 of 20

Take a Walking Tour of Back Bay

Charles River

TripSavvy / Violet Smirnova

Start with a walk along the Charles River to take in the beauty of this historic neighborhood near downtown Boston. Enjoy a quiet stroll down Commonwealth Avenue, admiring the brownstones that dot this tree-lined street modeled after Paris’ Haussmann renovation. Continue south to shop along trendy Newbury and Boylston streets. If you prefer a bit of guidance, ​free walking tours are available almost year-round.

12 of 20

Relax at Boston Common

Boston Common

 TripSavvy / Violet Smirnova

The oldest city park in the United States—established 1634—the Boston Common consists of 50 acres between Charles Street and Downtown Boston. Originally used to graze cattle, the Common is now the place for Bostonians to come to graze during a lunch break or a weekend picnic. The Common is also the beginning of the Freedom Trail, making it the perfect place to sit for a while after walking it. When winter arrives, ice skating is available at the Boston Common Frog Pond.



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13 of 20

Take in the History of the Boston Public Library

Inside the main reading room in the Boston Public Library

 TripSavvy / Taylor Nealand

While a trip to a public library may not rank highly on everyone’s vacation to-do list, the Boston Public Library is a must-see for visitors thanks to its many prominent murals, huge reading rooms, and Italian Renaissance-inspired interior courtyard complete with fountains and arched pathways. The library also hosts unique, free events throughout the year, ranging from readings to theater performances. 


14 of 20

Relive the 1960s at the John F. Kennedy Presidential Library and Museum

The entrance to the JFK presidential library

TripSavvy / Violet Smirnova 

President John F. Kennedy's library and museum offers a glimpse into the 1960s and a chance to experience the life of the president firsthand. While Kennedy only spent a thousand days in office, the museum is home to more than 20 multimedia exhibits and period settings from the White House. I.M. Pei designed the memorial, which sits on a 10-acre waterfront site on Columbia Point. From there, you can see Boston's skyline and nearby Harbor Islands. 

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See Ballet at the Boston Opera House

Boston Opera House

 Getty Images

Initially built in 1928 as a movie palace, the Citizens Bank Opera House lay empty from 1991 to 2004. Following a massive restoration and refurbishment, the Boston Opera House became home to the Boston Ballet. The ornate theatre is also the place to catch touring Broadway shows as well as their annual production of The Nutcracker each holiday season. 

16 of 20

Catch a Celtics Game at TD Garden

TD Garden

TripSavvy / Violet Smirnova 

For the true sports fanatic, consider an afternoon Red Sox game at Fenway and then head over to TD Garden at night to catch a Celtics game. The stadium is located about three miles from Fenway in Boston’s West End. If the NBA season isn’t in full swing yet, the Garden is also home to the Boston Bruins hockey team and hosts concerts year-long.

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17 of 20

Hover Over Boston Harbor at the Institute for Contemporary Art

Institute for Contemporary Art

TripSavvy / Violet Smirnova 

One of the best pieces at the Institute of Contemporary Art? The building itself. This South Boston museum is housed in a modern piece of glass architecture that contrasts the rest of Boston’s historic buildings. A highlight is the rear of the museum, a cantilevered glass expanse that hovers over Boston Harbor.

18 of 20

Visit the Prudential Skywalk

Boston cityscape from the Skywalk Observatory of the Prudential Center
Sen LI / Getty Images

After 200 Clarendon (formerly known as the John Hancock building) closed their observation deck as a result of the Sept. 11 terrorist attacks, the city of Boston lost their greatest view, but visitors and residents can now enjoy panoramic views from the city’s second tallest building, the Prudential Center, located in Back Bay. Don’t worry if you don’t know every Boston hotspot; the Skywalk provides headphones to listen to a free audio tour about sights as well as Boston history and culture as you walk around. In addition, telescopes are available to enhance your Boston sightseeing experience.

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Support Local Productions at Huntington Theatre

Exterior of the Huntington theatre company

TripSavvy / Violet Smirnova

Boston’s leading professional theatre since 1982, the Huntington theatre has won the Tony award for "Best Regional Theater" and more than 150 Elliot Norton and Independent Reviewers of New England Awards. Since its opening, the Huntington has played to over 3.5 million people, and presented more than 200 plays—18 of which went on to Broadway or off-Broadway.

20 of 20

Have a Toast at "Cheers"

Cutouts at the original Cheers bar

 TripSavvy / Taylor Nealand 

Famous as the inspiration for the television show Cheers, the former Bull & Finch Pub, now officially known as Cheers Boston, is located in Boston's Beacon Hill District. It's definitely a tourist trap with souvenirs galore for sale and overpriced pub food, but it's still one of those places that fans of the show make a beeline for when they're in Boston. There's a second replica of TV's most famous bar now, too, at Faneuil Hall Marketplace.

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