How to Explore Boston Like a Local: the Restaurants, Bars & Activities to Enjoy on Your Next Trip

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The Modern Travel Agency


  • Boston

  • Massachusetts

One of our favorite things at Fora is meeting up with local advisors in their home cities. Following a recent get-together in Boston — filled with hotel inspections, lots of food and perhaps a few cocktails — we recruited some of our expert Boston advisors for their top recommendations on what to eat, drink and do in this charming city.

Read on for their insider tips. Then connect with Fora to plan your Boston getaway today.

The top restaurants in Boston, from authentic Italian to stylish Greek

Image courtesy of the Newbury Boston

Boston’s food scene is vibrant, with a confluence of cultures making it especially exciting. 

Of course, you cannot visit the city without sampling some of its A+ Italian food. Fora Advisor Noelle Rudloff recommends Carmelina’s, in Boston’s North End (i.e., Italian) neighborhood. 

“Carmelina’s stands out for consistently wonderful Italian comfort food dishes,” she says. 

Favorites include the Sunday macaroni, the bolognese and little neck clams. And although Carmelina’s reserves a few spots for walk-ins, reservations are highly recommended. According to Noelle, the restaurant is ideal both for family meals and date nights: “I have been taking my daughters here since they were toddlers,” she says.

More North End gems include the family-owned Massimino’s, for super authentic Italian, and Caffé Vittoria, for the best espresso martinis, says Fora Advisor Dahlia Swerdloff.

Another Italian favorite of Dahlia’s is Contessa, on the rooftop of the trendy Newbury hotel.

The restaurant “has the most beautiful aesthetic, amazing Italian food and such a cool vibe,” she says.

The Newbury is also home to the Street Bar, a favorite of Noelle’s for an “old-school Boston” experience.

“Many a cold, rainy Boston night, I have curled myself around an Old Fashioned in this cozy Boston bar that looks out into the Boston Public Garden,” she says.

Another cozy, handsome hotel bar — Rowes Wharf Bar — can be found at the Boston Harbor Hotel. 

“There is nothing better than a sophisticated and sexy hotel bar with deep leather chairs that make you want to order a cocktail, stay awhile, then order another,” Noelle says, adding how it’s “the perfect place for date nights, catching up with old friends or having a nightcap.”

It’s also perfect for whiskey-lovers (herself included), she notes, as well as for cocktails — both classic and inventive.  

For out-of-this-world Greek food, head to Krasi, a top recommendation from Noelle and Fora Advisor Natalie Kurtzman, who loves sitting at the restaurant’s sleek, intimate bar.  

“The salads and vegetables are inventive and amazing,” Noelle says. “Try their tzatziki, smoked octopus and Souvla, a Greek rotisserie that changes daily.”

For lively nights out with friends, Natalie loves Nautilus for excellent pan-Asian cuisine, and Yvonne's for shareable Mediterranean-inspired plates. Loco Taqueria & Oyster Bar is also always a good time. Go for the coconut margaritas, Natalie advises. 

This is Boston, after all, and the seafood is among the country’s best. Natalie recommends Select Oyster Bar, where everything is fresher than fresh. And because Boston’s oyster scene is unparalleled, also try Neptune Oyster Bar, one of Noelle’s go-to’s.

“Don't miss the burger topped with fried oysters,” Noelle says.

And then there’s dessert. The chic Tatte Bakery is famous for a reason (“You can't go wrong with any of the croissants or pastries,” says Dahlia), with several locations throughout the city. And Picco, a lively neighborhood pizza joint, serves up some delicious ice cream, says Natalie.

Fora Perks at the Newbury Boston:

  • $100 food / beverage credit.

  • Breakfast daily.

  • Upgrade and extended check-in/out whenever possible.

Fora Perks at the Boston Harbor Hotel:

  • $100 hotel / resort credit.

  • Breakfast daily.

  • Upgrade and extended check-in/out whenever possible.

The best things to do in Boston: museums, parks & embracing the seasons

Isabella Stewart Gardner Museum

There are numerous things to see and do in Boston: museums, shopping, gardens, parks. And because of the city’s relatively small size, you can easily fit in a lot.

Noelle recommends the Isabella Stewart Gardner Museum, “a little jewel box of a museum housed in a Venetian-style palazzo in Boston's Fenway neighborhood.”

Here you’ll find a collection of the art collector’s own work. Noelle shared how some of Gardner’s most famous pieces were stolen in an infamous heist, in 1990. Other artists on display include John Singer Sargent, Botticelli and Titian. 

“The courtyard garden is a revelation,” Noelle says, “bringing thoughts of summer on even the dreariest Boston days.”

Speaking of summer, Natalie emphasizes how Boston is all about the seasons. In the summer, you’ll find her “taking water taxis, enjoying live music outdoors and spending time with friends.”

Hop on a swan boat or wander through the Rose Fitzgerald Kennedy Greenway, a modern park with food trucks, carousels, art, fountains, beer gardens and so much more. Dahlia loves running along the Charles River, and says the Seaport area is perfect for exploring. The district’s highlights include the Boston Children's Museum (“one of the best!” says Dahlia), the New England Aquarium and the Museum of Science, Boston.

In the fall, get cozy at spots like Beacon Hill Books & Café, says Natalie. And in the winter, prepare for snow — and for all the coziest holiday activities (caroling, gingerbread-house making, seeing The Nutcracker). 

“I love sledding in our neighborhood and going ice skating at the frog pond, followed by hot chocolate,” Natalie says. We’re already there.

Ready to travel? Connect with Fora to plan your Boston getaway today.

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