Visiting Boston for the First Time? Here’s What To See and Do

For history buffs and curious travelers alike, the 2.5-mile (4-kilometer) Freedom Trail should be your first stop in Boston. This walking route takes you to historical monuments sprinkled around the city, and is best traversed on a guided tour so you can learn more about its significance.

Stop at Boston Freedom Trail highlights such as the Old State House, Granary Burying Ground, and the Old North Church, which played an important role in Paul Revere’s midnight ride that began the Revolutionary War. A tour of the trail typically takes 90 minutes, so there’s still plenty of time to fit other activities into your day.

Fenway Park, where the Red Sox baseball team plays, is a significant landmark in a city known for its unabashed sports fandom. Even if you don’t want to watch a whole game, the stadium is worth a stop on a hop-on-hop-off trolley excursion or maybe even a guided ballpark tour to see the Green Monster and Pesky Pole. On game day, make sure to check out Jersey Street next to the park, which becomes an open-air market of sorts where you’ll find excellent street food, live entertainment, and Red Sox merchandise.

There are lots of museums and historic sites in Boston to visit on a rainy or snowy day. Start with the global collection on display at the Museum of Fine Arts or take the kids to the Boston Museum of Science for a day of hands-on discovery.

Meanwhile, the Isabella Stewart Gardner Museum is worth a visit just for the Venetian courtyard if not for its quirky art collection. Though not a museum, exactly, the New England Aquarium is still one of the top things to do in Boston, Massachusetts, and a great option for a first-time visit when you want to escape the cold.

Don’t visit the city for the first time without making the most of the Boston Harbor and its waterfront activities. There are a number of different options to suit different kinds of visitors, such as sailing around the harbor and its islands, taking a sunset dinner cruise, or even hopping on a duck boat tour that explores the city by land before plunging into the water. And if you’re wondering how to get around Boston without a car, keep in mind that you can catch a ferry to many destinations from the Boston Harbor.

Any 1- or 2-day itinerary for visiting Boston should include some time in the North End. Step into this district and you might imagine you’re actually in Europe. That’s because the neighborhood, which functions as the city’s Little Italy, has narrow alleyways, cobblestone streets, and an abundance of Italian restaurants and shops.

The best way to experience its cultural and culinary heritage is on a North End food tour, during which a guide will take you to the top restaurants and street food destinations, including Mike’s Pastry where tasting a cannoli is a must. Keep in mind this is also one of the best neighborhoods to stay in Boston.

One of the most significant events that set the Revolutionary War into motion was the Boston Tea Party of 1773, when Bostonians stole chests of tea from several tea ships and threw them into the harbor in protest of British taxation.

While in Boston, you can reenact this event for yourself when you visit the Boston Tea Party Ships & Museum and learn more about the significance of this turning point in American history on a guided history tour. It’s one of the most family-friendly attractions in Boston, both fun and educational for visitors of all ages.

If you’re visiting Boston for the first time during the summer (June through August), go on a whale-watching tour to see these incredible marine beasts in action.

The Stellwagen Bank National Marine Sanctuary, located just off the coast, forms popular feeding grounds for humpback, fin, and minke whales as well as dolphins, so you have a high chance of a sighting. Since the marine reserve is only a short speedboat ride from Boston, you can make whale watching part of a larger itinerary, even if you’re short on time—it’s definitely worth the trip.

Get your food with a side of history when you visit Faneuil Hall and Quincy Market. Faneuil Hall was built in 1742, and served as a meeting place and market, earning the nickname “Cradle of Liberty” because it’s where patriots led protests.

In 1826, it was expanded into a full public market (Quincy Market), and now has become a food hall and commerce hub, home to street performers, shops, and stands where you can grab classic New England dishes, including lobster rolls. If you’re wondering where to eat seafood and clam chowder in Boston, start here.

Boston Common is America’s oldest park, dating all the way back to 1634. For years, it was used for cattle grazing, and then for training soldiers during the Revolutionary War—so it’s filled with important historical monuments.

Now, you can visit the area with a picnic, check out the public gardens next door, ice skate on Frog Pond in the winter, see the Edgar Allan Poe statue, or use the spot as the starting point for the Freedom Trail. The Common is a true oasis in the city and an ideal place to go when you need to get back to nature.

When visiting Boston for the first time, you have your pick of interesting neighborhoods and suburbs, and Cambridge is one of the best. This area, home to Harvard and MIT, is highly walkable—it’s ideal for a stroll along the Charles River, gathering in the Cambridge Common, checking out the street scene in Harvard Square, or simply wandering the old cobblestone streets, stopping by college cafés and bookstores. This part of the city is where a highly academic and modern urban scene meet, which makes for an interesting atmosphere and great people-watching.

Whether you’re looking for a place to get some work done or you’re curious to see one of Boston’s most impressive architectural landmarks, head to the Boston Public Library, a few minutes away from Back Bay Station.

This building, which is the main branch of the library, boasts an enormous reading room with a vaulted ceiling, a grand staircase, and a peaceful courtyard. You can sit in the public spaces or check out 19th-century art that covers the walls and ceilings inside. The library also regularly hosts free cultural and community events, which you may catch if the timing is right.