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5 Awesome Things to Do in Boston This Summer

The summer can feel unbelievably brief in New England. Now that warm weather is finally here, it’s time to step outside and take advantage of everything Boston has to offer. Here are some of our favorite experiences in and out of the city this season.

Stroll the North End

Boston’s North End neighborhood is home to one of the largest Italian-American populations in New England. Not surprisingly, the tiny enclave also features the highest concentration of (amazing) Italian restaurants in the area as well. Ambling the neighborhood end to end requires little more than an hour — but allow a lot more time if you plan to eat your way through town. Highlights include Regina Pizzeria (the city’s oldest and arguably most iconic pizzeria) and Ernesto’s (a neighborhood institution that’s used the same pizza recipes for more than 30 years).

Drink and Dine Alfresco

Bostonians know how to squeeze every last bit of enjoyment out of the summer season. For many, that means eating outdoors as much possible. The city offers scores of great rooftop patios, beer gardens and waterfront spots. For a no-frills, locals-friendly watering hole, The Baseball Tavern offers one of the city’s oldest rooftop decks with excellent views of Fenway Park. For an upscale alternative with great cocktails, check out the chic, South Beach-inspired pool deck at The Colonnade Hotel.

Spend the Night in Jail

Kitschy, themed hotels are nothing new. But spending the night in a former-jail-turned-luxury hotel is an entirely unique experience. The Liberty Hotel offers beautiful, four-star accommodations, and its stunning lobby previously served as the heart of the city’s most infamous prison. The appropriately named CLINK. restaurant and bar is also a great place to grab brunch on Sunday mornings. Be sure to ask for a table inside one of the renovated jail cells. The property is ideally located less than five minutes from the Charles River and chic restaurants and shops of Beacon Hill.

Grab a Drink at the Top of the Hub

The majority of Bostonians would likely turn their noses up at the thought of cocktails at the Top of the Hub. It’s a shame, really, because Boston’s highest bar not surprisingly offers some of the best aerial views of the city. Cocktails aren’t cheap (there’s actually a $24 minimum tab per patron after 8pm), but the stunning views more than make up for the steep prices. Even if it does feel a bit touristy, know that the tourists are all coming here for a very good reason.

… Or Just Get Out of the City

Sometimes the best thing to do on a hot summer day is just get out of the city. Provincetown is one of the quaintest, most picturesque towns, not only in Massachusetts but in the entire Northeast. At nearly three hours from Boston, the often bumper-to-bumper drive can prove frustrating for unseasoned New England road trippers. The best way to escape the city to P-town is via the Cape Cod Fast Ferry. Not only does the 90-minute ride cut the total transportation time in half, it’s arguably one of the best ways to see the state and its stunning coastline.

Mike Richard

5 Awesome Things to Do in Boston This Summer from Boston Things to Do


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