Things to Do in Boston: 72-Hour Guide

Planning a quick trip to Boston? There’s a lot of cool stuff to do and see while you’re in town. Here’s a 72-hour guide to point you in the right direction.

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More than 18 million people visit Boston every year for history, culture, and a dazzling array of attractions, restaurants, and nightlife. If you’re one of the millions planning a trip to Boston this year, then congratulations. You’re going to experience one of America’s greatest cities. To get the most out of your time, balance your itinerary between historic sites, city hotspots, and world-famous eats. Here’s a sample weekend-in-the-life.

A portion of the red brick line along the Freedom Trail in Boston, Massachusetts.

Day 1

After you check in to your hotel, head out and explore some of Boston’s famed historical sites. With so much history to see in Beantown, there’s no time to waste.

Do: Walk the Freedom Trail

Have you noticed the red-painted line in downtown Boston? That’s no roadwork mistake; it means you’re on the Freedom Trail, a 2.5-mile route that takes you past 16 historical sites.

Costumed guides offer tours throughout the day from both the Boston Common Visitor Center and the ArtsBoston booth at Faneuil Hall. En route, you pass by Massachusetts State House, Park Street Church, Granary Burying Ground, the Boston Massacre site, and more.

Eat: Gourmet Dumpling House

Not far from the Chinatown gate you’ll find Gourmet Dumpling House, one of Boston’s most raved-about Chinese dim sum restaurants. Fill up on soup dumplings, pork dumplings, and sticky buns. Leave room for delicacies such as sliced fish Sichuan style or a chef’s special. Be prepared to wait for a table — the restaurant draws healthy crowds.

Do: Visit a Reenactment

Boston and the surrounding areas host dozens of re-enactments throughout the year, most notably to honor Patriots’ Day in April, which commemorates events and battles that marked the beginning of the Revolutionary War. There is also a re-enactment of the Boston Tea Party each year on December 16.

Many historical sites host regular re-enactments and interactive tours. From June to October, the Old State House is filled with costumed actors portraying historical figures, and you can step aboard a ship and feel like you’re back in 1773 at the Boston Tea Party Ships and Museum.

Eat: Cheers

Cheers is a favorite among Boston tourists. The Boston pub that inspired the hit TV show is located on Beacon Hill, not far from Boston Common. Opened in 1969 as the Bull & Finch Pub, Cheers offers the pub fare you’d expect: burgers, sandwiches, and a few hearty entrees. Top picks include the Burger Meister, a burger topped with mushrooms and Muenster cheese; and Coach’s Club Sandwich, which is packed with ham, turkey, and bacon.

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Good to Know: Cheers has a second location at Faneuil Hall Marketplace.

A view of the Harvard Yard in Cambridge with green grass and autumn foliage on a sunny afternoon.

Day 2

Hopefully you set your alarm for an early start so you can get your fill of Boston’s distinct ambiance. Feeling like getting a little exercise in? Head to Boston Common in the morning for an easy run along the Charles River.

Do: Visit Harvard Yard

The Boston area is an academic powerhouse, with respected institutions such as Harvard University and MIT located minutes from Boston. To get a glimpse of Ivy League life, take a stroll around Harvard Yard. Stop at Memorial Church, Memorial Hall, and the John Harvard Statue. If time permits, visit Peabody Museum for archaeological finds and the Arthur M. Sackler Museum, both on campus.

Eat: Harvest

While you’re in Cambridge, check out the restaurant where students take their parents. Harvest features local, seasonal cuisine and a gorgeous outdoor patio. Try the Garlic and Chickpea Falafel Sandwich or a warming bowl of butternut squash soup.

Eat: North End

Alternatively, if you’re in the mood for Italian fare, head to the North End, Boston’s Little Italy. More than 80 restaurants back these narrow blocks, so you’re bound to find a pasta dish that pleases. Top spots include Rabias (Salem Street), Pagliuca’s (Parmenter Street), and Prezza (Fleet Street).

Do: Experience Boston’s Nightlife

Whether you want to dance the night away or see a show at one of Boston’s theaters, you’re sure to find something to suit your style. From comedy clubs and nightclubs to sports fields and concert venues, there’s something for everyone when it comes to this city’s rocking nightlife.

A close up view of penne pasta in a white bowl at a restaurant in Boston's Little Italy neighborhood.

Day 3

You’re in the homestretch of your Boston trip. Try to fill your itinerary with as many quintessential Boston experiences as possible to make the most of the time you have left.

Do: See the Red Sox at Fenway Park

It’s been among the country’s favorite stadiums for more than a century, and it’s been a favorite stop for Red Sox fans since opening in 1912. If you’re lucky enough to catch a game, awesome. If not, you can still take a tour of what’s known as “America’s Most Beloved Stadium.”

Eat: Mike’s Pastries

Treat yourself to some cannolis at Mike’s Pastry, and channel your inner Italian. A North End tradition since 1946, visitors and Bostonians alike rave about Mike’s pastries and cookies.

Do: Take a Tour

Sometimes, the best way to see the nooks and crannies of a city is by signing up for a tour. Whether you prefer walking, cruising, or hopping on a Segway, Boston’s best tours offer something for everyone, including unique experiences like these:

  • Hop a lobster boat for a trap-to-table lobster experience with Boston Lobster Tours.

  • Ogle art and architecture on a free Boston Public Library Tour.

  • Get a dose of Boston’s culture on your own timetable with a hop-on, hop-off Trolley Tour.

Good to Know Before You Go

Book your hotel far in advance, especially if you’re planning to visit on a holiday or during a big event like the Boston Marathon. When you’re choosing a hotel, consider the location. For example, the opulent XV Beacon is right near Boston Common while Boston Harbor Hotel is located right at Rowes Wharf. But don’t overlook staying a little farther out, especially if the hotel is near a shuttle that can take you anywhere you want to go. Check the MTBA website for schedules and information.

Prepping for your next big trip? Check out our travel guides on Pinterest for a little inspo before hitting the road!

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