10 Best Things to Do in Boston This Summer 2025

Looking for the best things to do in Boston this summer? Whether you’re craving city-spanning adventures, sky-high relaxation, or flavors from around the globe, this curated list of 10 can’t-miss experiences has you covered. From feasting in the North End and catching Shakespeare under the stars to pedaling through the Emerald Necklace or sipping cocktails on a tiki boat, these are the most unforgettable ways to soak up summer in the Hub—whatever your perfect day looks like.

10 Best Things to Do in Boston This Summer

1. Join the Party in the North End – Celebrate Italian heritage at Boston’s lively summer street festas.

The colorful, flavorful, and semi-chaotic glory of the North End’s festas (or feast days) celebrates the southern Italian heritage of honoring beloved saints and martyrs with processions, music, food, and prayer. Streets fill with revelers, live music echoes off brick buildings, and the air is scented with savory sausage and peppers. Two of the largest are the Fisherman’s Feast, August 14–17, and Saint Anthony’s Feast, August 28–31, but all are worth checking out.

2. Dine by the Water in Eastie – Savor Italian fare with million-dollar skyline views.

The best-kept secret in waterfront dining is East Boston, where the million-dollar views of Boston’s skyline seem to outshine any other on the harbor. Water taxis board at Fan Pier or Long Wharf on the Boston side and disembark on the Eastie side just steps from Mida, chef Douglass Williams’s award-winning Italian restaurant, where the meatballs, gnocchi cacio e pepe, and clam pizza hold their own against the scenery.

3. Pedal the Parks – Explore Boston’s green gems by bike on a guided or DIY ride.

Don’t get so distracted by the harbor’s sapphire waters that you forget the city’s Emerald Necklace. Urban AdvenTours runs a four-hour guided bike tour through the beautiful string of parks designed by Frederick Law Olmsted. From the Esplanade to the Southwest Corridor Park and the Arnold Arboretum, you’ll cover more than 15 miles and several of the city’s most beloved urban oases. Or, strike out on your own with a rented e-bike from the network of Bluebikes parked all over Boston, and you’ll barely break a sweat.

4. Soak Up Free Culture – Enjoy outdoor concerts and Shakespeare under the stars.

The Boston Landmarks Orchestra hosts open-air concerts at the Hatch Shell throughout the summer. Grab snacks and a beer before the show at the Esplanade’s Night Shift Brewing beer garden. Alternatively, Free Shakespeare on the Common presents performances of As You Like It from mid-July through early August on Boston Common. Nab picnic supplies at the newly opened Flour Bakery at the nearby Concession Pavilion and savor a repast beneath the stars.

5. Catch a Tropical Wave – Sip tiki cocktails while cruising Boston Harbor.

Tiki Boat Boston operates a fleet of three pontoon boats, all decked out in full tiki bar fashion with palm roofs and tropical silk flowers arranged around a full bar complete with bartender and DJ. Parties of up to 24 can sip mai tais and palomas while cruising Boston Harbor and soaking up views of iconic landmarks on the 90-minute trip. Private and corporate reservations are available, too.

6. Get Your Licks In – Take a scoop-filled tour of Boston’s best ice cream spots.

Take inspiration from the Massachusetts Ice Cream Trail, which highlights 100-plus sweet spots across the state, to plot your own scoop-filled journey across Greater Boston. Emack and Bolio’s in Charlestown and the Back Bay, Gracie’s in Somerville, and Honeycomb Creamery in Cambridge are all worth a visit, along with locally owned mainstays like New City Microcreamery, Toscanini’s, and Christina’s in Cambridge; Boston Ice Cream Factory in Dorchester; Crescent Ridge at the Boston Public Market; and vegan specialist FoMu in the South End, Fenway, and Quincy Market.

7. Take a Sky-High Dip – Lounge poolside above the city at the Colonnade Hotel.

The Colonnade Hotel boasts a lovely rooftop pool with views of the Back Bay and the South End, food and drink service, and cabanas to rent. It’s open to the public Monday through Thursday and on Sunday afternoons for a fee of $55, which seems fair for a full day of waterside luxury in the heart of the city.

8. Chow Down in Chinatown – Eat your way through a neighborhood rich in flavor and history.

Along with roughly 7,000 residents, Chinatown is home to legacy eateries and newcomers, plus bakeries, barbecue spots, and enough other treasures to fill a weekend itinerary. Boston Chinatown Tours, led by longtime resident Jacqueline Church, takes you to the best of the best, with delicious bites and deep insights along the way.

9. Go ‘Fourth’ and Conquer – Celebrate Independence Day the Boston way.

There’s more to Independence Day in Boston than the Pops and fireworks. Attend the annual reading of the Declaration of Independence from the balcony of the Old State House in the morning, then head to the Seaport to view the turnaround cruise of the USS Constitution. In the afternoon, head to Downtown Crossing for an ice cream social and the reading of Frederick Douglass’s electric 1852 speech “What to the Slave Is the Fourth of July?”

10. Roll with It – Enjoy the ultimate lobster roll with harbor views to match.

A great lobster roll eaten by the water is the ultimate expression of the form. ReelHouse Oyster Bar sits at the very end of Fan Pier, and its lobster roll, served cold with mayo or hot with butter, is excellent. The restaurant is upscale, with seafood towers and caviar service (along with Neapolitan-style pizzas for the seafood-averse). Looking for a seafood-shack vibe? James Hook & Co. has all the classics—hot and cold rolls, lobster pie, chowder—just a stone’s throw from the spot where Fort Point Channel meets the harbor.

See More: 2025 Boston Travel Guide | Hotels, Dining & Attractions

What tops your list of the best things to do in Boston this summer? Let us know!

Amy Traverso

Amy Traverso is the senior food editor at Yankee magazine and co-host of the public television series Weekends with Yankee, a coproduction with WGBH. Previously, she was food editor at Boston magazine and an associate food editor at Sunset magazine. Her work has also been published in The Boston Globe, Saveur, and Travel & Leisure, and she has appeared on Hallmark Home & Family, The Martha Stewart Show, Throwdown with Bobby Flay, and Gordon Ramsay’s Kitchen Nightmares. Amy is the author of The Apple Lover’s Cookbook, which was a finalist for the Julia Child Award for best first-time author and won an IACP Cookbook Award in the “American” category.

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