Boston — the capital city of Massachusetts — has the perfect blend of old and new. Modern skyscrapers stand imposingly over colonial buildings, and activities range from historic sightseeing to exploring the Museum of Science. The city played an important part in the American Revolution, and you can trace history through the famous Freedom Trail or by visiting a living museum at Plimoth Plantation.
However, you don’t need to be a history buff to enjoy a city break in Boston — its waterside location provides sailing and whale-watching opportunities, and there are plenty of family-friendly activities, from the Boston Children’s Museum to the LEGOLAND Discovery Center.
If you’re flying into Boston for your city break, take a look at our guide to Boston Logan International Airport (BOS) for information about the terminals, airlines, ground transportation, and more.
Historical Things to Do in Boston
1. Learn About the Battle of Bunker Hill
Bunker Hill Monument commemorates the 1775 battle between New England soldiers and the British Army during the early period of the American Revolutionary War. The 221-foot obelisk was constructed from quarried granite and stands on what is now known as Breed’s Hill. A statue of Colonel William Prescott — who led the New England soldiers — stands in front of the monument. There’s also an adjacent museum featuring a 360-degree cyclorama mural depicting the battle, along with various artifacts.
2. Experience the Boston Tea Party on Board a Replica Ship
Journey back to 1773 and learn about one of the most important events leading up to the American Revolution. The Boston Tea Party Ships and Museum is a truly immersive experience, with live reenactments, interactive exhibits, and multi-sensory films. You’ll meet one of the Founding Fathers of the U.S. — Samuel Adams — and will take part in the destruction of the tea.
Book your interactive tour here with 24-hour cancellation.
Hot Tip: If you’re visiting Boston from the Big Apple for business or pleasure, check out our guide on the best ways to travel from New York City to Boston.
3. Visit the Historic Home of Paul Revere
Paul Revere House is the oldest house in downtown Boston, having been built around 1680. The house was owned by the patriot and silversmith Paul Revere from 1770 to 1800 and was the location from which he left on his famous midnight ride to warn John Hancock and Samuel Adams of their impending arrest by the British.
4. Take a Tour of Harvard University
Harvard is one of the oldest learning institutions in the U.S., and you can enjoy a guided tour of the campus to learn all about the history of this illustrious university. Tours are led by enthusiastic students who will tell you all about the campus culture and their own personal experiences, and you’ll get to visit the likes of Harvard Square, Johnston Gate, and Cambridge Common.
5. March on Board the USS Constitution
The USS Constitution, or “Old Ironsides” as she’s also known, is the oldest commissioned ship in the U.S. Navy. With a seemingly impenetrable hull, the USS Constitution defeated 4 British warships during the War of 1812, along with numerous other triumphs. Meet the crew onboard the ship before heading to the USS Constitution Museum to delve into the ship’s history with artifacts and interactive exhibits.
The Best Free Things to Do in Boston
6. See the Sights of the Freedom Trail
The Freedom Trail is a 2.5-mile red-brick path that guides visitors to 16 of the city’s most important historical sights. The route takes you to significant churches, museums, parks, ships, and meeting houses that all played a part in the American Revolution. Many of the sites along the route are free to visit, including Boston Common, Granary Burying Ground, and the Bunker Hill Monument.
Explore the Freedom Trail at your own pace with a self-guided app tour or book a tour with a costumed guide to tell you all about the different landmarks.
Hot Tip: If you’re planning on walking the entire length of the Freedom Trail, be sure to take a good pair of walking shoes with you.
7. Stroll Around Castle Island
Castle Island is no longer an island, but a peninsula located in South Boston. The 22-acre area has a harbor walkway perfect for a stroll or rollerblading, a beach, a children’s playground, a snack bar, and excellent views across to Boston Harbor and Boston Logan International Airport.
Fort Independence can be found on Castle Island, and you can enjoy a free 20-minute tour on Saturday or Sunday between 12 p.m. and 3:30 p.m.
8. Reflect on the Atrocities of the Holocaust
The New England Holocaust Memorial is located in Carmen Park and was built in remembrance of the millions of Jews that were murdered in the Holocaust. 6 glass towers are named after the 6 major death camps, with millions of numbers etched into the glass panels representing the harrowing ledger of its victims. Reflect as you walk along the granite walkway beneath the towers and read powerful messages from its survivors.
9. Visit the Boston Public Library
The Boston Public Library is another historic landmark and is located across from Copley Square. Inside and out, the building is an architectural gem, with its arcaded windows, barrel-vaulted ceilings, and a grand open-air courtyard. Home to many artistic treasures, the library offers free art and architectural tours to learn about these significant pieces, including the stunning murals by French artist Pierre Puvis de Chavanne.
10. Explore a Park With a Deep-Rooted History
Founded in 1634, Boston Common is one of the oldest parks in the U.S., historically serving as a location for public punishments of pirates and witches and used as a military camp for the British Redcoats. The common has played host to many public gatherings, including anti-Vietnam War protests and civil rights rallies, and provides a relaxing green space full of sculptures and memorials to reflect on its varied past.
Best Things to Do in Boston in the Summer
11. Explore the City by Land and Water With a Duck Tour
Explore the city by land and water with Boston Duck Tours. These amphibious vehicles were used in World War II and will take you past sights such as Boston Common and Quincy Market before cruising down the Charles River to see Boston and Cambridge from the water. You’ll have your very own “ConDUCKtor” to tell you all about the history of the important landmarks that you’ll pass.
12. Cruise Around Boston Harbor
There’s no better way to appreciate the impressive Boston skyline than with a harbor cruise. Many cruise types are available, including romantic sunset cruises, brunches, live music, or BBQ, and beer cruises. If you’re looking to explore the history of Boston Harbor, jump on board a sightseeing cruise with narration from your guide as you pass attractions such as Fort Independence, the USS Constitution, and Spectacle Island.
13. Mingle With the Pilgrims at a Living Museum
Plimoth Plantation is a living museum where costumed actors reenact the lives of a 17th-century colonial English village. Step back in time as you wander around the village and engage with the townspeople as they go about their everyday lives, farming, cooking, and caring for their children.
Along the Eel River banks is a Wampanoag Homesite where native people dressed in traditional Wampanoag clothing will chat with you about how their people would have lived in the 17th century. There’s also a full-scale replica tall ship and corn grinding mill to explore.
Book your ticket here with a 24-hour cancellation policy.
Hot Tip: Plimoth Plantation is around 45 miles south of Boston, or just over an hour by bus. Alternatively, if you choose to rent a car, take a look at our guide to the best car rental agencies.
14. Go Whale Watching
The best time to spot whales around Boston is spring through early fall when migrating whales head to Stellwagen Bank National Marine Sanctuary’s rich feeding grounds. Many operators set sail daily in search of humpback whales, minke whales, and fin whales, while there’s also the opportunity to spot dolphins and sea birds.
15. Hop on and off a Trolley Tour of the City
A trolley tour is a fantastic way to see Boston, as it covers just about every historical attraction and landmark while you listen to the narration from the friendly trolley conductors. Tours explore all the significant areas, including downtown, Back Bay, Beacon Hill, the theater district, and the waterfront, and you can hop off at your leisure to explore a particular attraction in more detail.
Hot Tip: You’ll be passing a great number of iconic landmarks on your tour, so make sure you’ve got the perfect travel camera to snap away.
Best Things to Do in Boston in the Winter
16. Go Ice Skating at Boston Common
From November to March, Frog Pond on Boston Common transforms into an ice-skating rink and is a magical location, especially during the festive season. Skate rentals are available from the concession stand, and you can warm up afterward with hot cocoa from the Frog Pond Cafe. If you need a bit of a helping hand to get started, group skating lessons take place Saturday, Sunday, and Mondays throughout the season.
Hot Tip: Although the ice skating rink is weather dependent, Frog Pond has its own ice-making system to help things along, so you can be pretty confident when booking tickets in advance.
17. Shop for Souvenirs at Faneuil Hall Marketplace
Faneuil Hall Marketplace is an excellent place to shop for gifts and souvenirs with a mix of brand name shops and small independent boutiques and stalls. Along with shopping, you can also grab a bite to eat at one of the 12 restaurants and pubs or at the Quincy Market Food Colonnade before enjoying entertainment from the street performers outside of the marketplace.
18. See a Show at Emerson Colonial Theatre
Having opened to the public in 1900, Emerson Colonial Theatre is the oldest continually opened theater in Boston. It often houses touring Broadway performances and has debuted productions such as Anything Goes, Oklahoma!, and La Cage aux Folles before they hit Broadway. The Emerson hosts a variety of performances, from shows to live music and comedy to speaker events.
19. Hit the Slopes at Blue Hills
The Blue Hills Reservation is located about 15 miles south of downtown Boston and has a small ski resort during the winter months. It’s a good option for beginners or those looking for a quick ski fix without driving hours out to the larger resorts. The 60-acre resort has 16 trails, 4 ski lifts, a terrain park, rental facilities, shops, and a cafeteria.
Hot Tip: If you decide to hit the mountains skiing, check out our ski and snowboard packing list.
20. Sample Some Craft Beer on a Brewery Tour
Boston has a thriving craft beer scene, and rather than just sampling some of the city’s favorites at a local bar, why not take a brewery tour to see how it all begins. Tour the Samuel Adams and Down the Road Beer Co. breweries before finishing at the Downeast Cider House where you’ll examine the brewing process, listen to a bit of history, and of course, get to sample some delicious ales and cider.
The Best Things to Do in Boston With Kids
21. Discover Over 700 Interactive Exhibits at the Museum of Science
The Museum of Science is one of the world’s largest science centers, attracting around 1.5 million visitors every year. Kids will love the range of permanent and interactive exhibits, including the Hall of Human Life, an Arctic Adventure: Exploring with Technology, and the Live Animal Care Center. The museum also has a domed IMAX theater and planetarium showing various educational films.
Skip the box office queues with this admission ticket.
Hot Tip: If you’re planning on visiting 4 or more Boston attractions, you can save 45% on admission with a Boston CityPass.
22. Zipline From a 33-Story Tower Building
If you’re looking for an exhilarating adventure, check out the HighFlyer Zipline that runs from the top of the Foxwood Casino for almost a mile to the Pequot Museum. You’ll reach speeds of up to 60 mph as you soar 350 feet above Connecticut forests, and with 4 parallel lines, your family can launch at the same time and race to the finish line.
For even more ideas, check out our detailed post about exploring Boston with kids.
23. See Colorful Corals at the New England Aquarium
Visit the New England Aquarium and discover over 600 species of aquatic life. The aquarium’s various exhibits have recreated habitats such as a tropical Caribbean ocean reef and the shallow tide pools of the Olympic northwest, which houses various species, such as sea turtles, stingrays, hermit crabs, and the giant Pacific octopus.
There’s a theatre showing short movies about the wonders of the natural world, and you can get up-close-and-personal with some of the aquarium’s inhabitants with an animal encounter.
24. Enjoy Exciting Exhibits at the Boston Children’s Museum
The Boston Children’s Museum is packed full of entertaining exhibits and hands-on experiences. As the second oldest children’s museum in the world, it’s been providing an environment for education and fun for over 100 years. The moment they walk into the museum, kids will love climbing the 3-story structure in the lobby, getting creative in the art lab, or exploring the authentic Japanese House.
25. Explore the Ultimate Indoor LEGO Playground
The LEGOLAND Discovery Center is the ultimate indoor lego playground for kids aged 3 to 10. At the model builder academy, kids will learn the best LEGO-building techniques from the experts, and in MINILAND, you’ll find some of Boston’s most iconic buildings constructed from LEGO. Hop onboard Kingdom Quest and zap beastly trolls or conjure a spell on Merlin’s Apprentice Ride.
Hot Tip: If you’re flying into Boston for your family city break, take a look at our guide to flying with children.
The Best Events in Boston
26. Don’t Miss the Boston July 4th Fireworks
The 4th of July is celebrated annually with the Boston Pops Concert at Hatch Shell, followed by a magnificent firework display. Half a million spectators come from all over the U.S. to gather at the banks of the Charles River to watch the Boston skyline light up. To avoid an obstructed view of the fireworks, get a spot early on the Harvard Bridge or along Storrow Drive.
Hot Tip: The 4th of July is an incredibly busy time in Boston, so you must book your accommodation well in advance to avoid disappointment.
27. Cheer on Rowers at the Head of the Charles Regatta
The Head of the Charles Regatta is a 2-day regatta that sees thousands of athletes rowing in competition for the honorary title of “Head of the River.” The 3-mile race takes place along the Charles River, with hundreds of thousands of spectators lining the water’s edge to cheer on competitors. Taking place in October, the views along the river are particularly beautiful, with its orange and red autumn foliage.
28. Party at the Boston Calling Music Festival
The Boston Calling Music Festival takes place in May at the Harvard Sports Complex in Alston. The annual music festival attracts around 40,000 festival-goers with previous performances from Eminem, Sia, Of Monsters and Men, Vampire Weekend, and many more. Music takes place across 2 stages, and there are lots of food vendors and activities in various tents across the event.
29. Support Runners at the Boston Marathon
The Boston Marathon is the world’s oldest annual marathon, having been first held in 1897. The 26.2-mile course starts in Hopkinton and ends on Boylston Street in Boston, and hundreds of thousands of excited spectators take to the streets to cheer on the weary runners. As the course follows quite a few subway stops, you could cheer on runners midway along the course before riding the subway to the end.
With the Boston Marathon taking place in April, the weather is usually fine, but make sure you’re prepared with the right clothing, just in case there’s a repeat of the chilly rain of 2018.
30. Take Part in the Annual Boston Tea Party Reenactment
On December 16, the Old South Meeting House and the Boston Tea Party Ships & Museum come together to relive one of the most important events in U.S. history. The Boston Tea Party reenactment starts with the famous debate in the Old South Meeting House (ticketed event) before crowds of people take to the streets to head down to Griffin Wharf for the dumping of the tea. Ticketed guests have guaranteed views of the ship, but the general public is also permitted to spectate.
Whether you chose to explore independently or join a guided tour, you’ll be sure to learn a lot about this fabulous city. If you time your visit right, you could be there to soak up the atmosphere of one of the city’s annual events, such as the 4th of July fireworks or the Boston Marathon.
If you’re visiting in spring or summer, the warm weather will allow you to immerse yourself in Boston’s waterside culture, or you can experience how incredible the city looks in fall with its colorful foliage.