3 Days in Boston

Colonial History, Contemporary Art, and Fresh Seafood

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The Old State House, which sits on Boston’s Freedom Trail, is a relatively short brick building between the skyscrapers of Boston.

WHEN Summer and Fall
WHERE Boston
HOW LONG 3 Days

This waterfront city is full of historic firsts and landmarks that predate the American Revolution. So it’s no surprise that one of the most popular things to do in Boston is travel back in time along The Freedom Trail, with stops including Faneuil Hall, Paul Revere’s home, and Boston Common, the first US public park. Another is visiting downtown Fenway Park, the only MLB stadium that still has a hand-operated scoreboard. Delve deeper, and you’ll uncover worthwhile contemporary attractions, preppy-chic hotels, and a pioneer spirit that lives on thanks to cutting-edge universities and a diverse cultural scene.

Compact and walkable, Boston and neighboring Cambridge are packed with appealing neighborhoods: the museum-lined harbor; the cobblestone streets and brownstones of Beacon Hill; the upscale shops of Newbury Street; and the North End with its Italian bakeries and oyster bars. Seafood is a must, and most corners of the globe are well represented at restaurants and food halls alike. When you’ve had your fill, Boston makes a great jumping-off point for a summer coastal road trip or exploring fall foliage in New England.

Start below with our recommended three-day Boston itinerary and learn about some of the benefits that you can enjoy throughout your journey when you book through American Express Travel®.

North End & Boston's Waterfront

Accommodation

The Langham, Boston

The Whitney

Mandarin Oriental, Boston

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Place of Interest

ICA Boston

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Eat & Drink

Woods Hill Pier 4

Neptune Oyster

O Ya

Mike's Pastry

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The Freedom Trail & Cambridge

Place of Interest

Step Back into Colonial History

Tour Harvard and MIT

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Eat & Drink

High Street Place

Oleana

Little Donkey

Pammy's

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Art & Baseball

Place of Interest

Isabella Stewart Gardner Museum

Museum of Fine Arts, Boston

Fenway Park Tour

Back Bay & Beacon Hill Neighborhoods

South End Shopping District

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Eat & Drink

Saltie Girl

Greystone Cafe, Bakery, and Provisions

Myers + Chang

Shore Leave

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Day 1: North End & Boston's Waterfront
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EAT & DRINK • DINNER

Meals That Are Worth the Wait

One pale hand squeezes lemon into an open oyster held by the other hand. A crystal goblet of light liquid is just out of focus behind.

Neptune Oyster

Be prepared to wait at this popular little oyster bar in Boston’s North End, where the line has been known to sneak around the corner. “All worth it,” say the devoted regulars. In addition to raw bar specialties and seafood towers, Neptune also excels at lobster rolls and Mediterranean-inspired main courses.

Overhead view of a round plate holding a steamer basket of ice. On the ice is an open oyster holding dark brown liquid and diced vegetables.

O Ya

If you’re in a celebratory mood, contemporary Japanese restaurant O Ya delivers with a 20-course omakase dinner that is one of Boston’s most satisfying splurges. The exquisite, flavor-packed dishes arrive one by one so that each gets its moment to be savored and appreciated.

Day 2: The Freedom Trail & Cambridge
Day 3: Art & Baseball
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PLACE OF INTEREST • MORNING

Immerse Yourself in Fine Art

The courtyard of the Isabella Stewart Gardner Museum is filled with bright greenery, scattered purple flowers, and italianate flourishes.

Isabella Stewart Gardner Museum

Modeled after Venetian Renaissance palaces, the former home of eccentric socialite Isabella Stewart Gardner makes a dazzling impression. Let yourself be charmed by the statues and greenery of the glass-encased courtyard and eventually make your way through the collection of artwork from legends like Matisse and Titian. If you notice empty frames, they are placeholders for paintings stolen in 1990—part of the greatest unsolved art theft in history.

Purchase Isabella Stewart Gardner Museum tickets online.

The Museum of Fine Arts, Boston, is a gray neoclassical building with banners displaying faces from global art and the word Welcome.

Museum of Fine Arts, Boston

The MFA’s comprehensive collection counts about 500,000 works that take you on a journey through time and space, from ancient Nubian art to contemporary North American masterpieces to the largest collection of Japanese art outside Japan. The museum caters to all comers, including children and the disabled.

Purchase MFA Boston tickets online.

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EAT & DRINK • DINNER

Get a Taste of the South Side

Overhead view of a pair of pale hands using a pair of spoons to dig into the fried egg atop a bowl of fried rice. Overhead view of a black-and-brown rectangular platter of browned dumplings, served with a bowl of red-brown sauce with green onions. Close-up of glazed salmon garnished with green onion and sitting on a bed of rice. Next to the plate is a Japanese newspaper and chopsticks.

Myers + Chang

In the South End of Boston awaits Myers + Chang, a family-style Asian diner with a cool vibe and dumplings that keep locals coming back for more. Wok-charred noodles with black bean sauce and the ginger, garlic, and pea fried rice are other forms of satisfying comfort food. Wash it all down with homemade pineapple vodka.

Book Myers + Chang on Resy and get special access when you add your eligible American Express® Card to your Resy profile. Terms apply. Learn More.

A table of thirtysomething adults of various races toast drinks, including several with umbrellas and one made to look like a coconut.

Shore Leave

Tiki torches are a sure sign that you’re leaving New England far behind and entering a tropical paradise, aka Shore Leave, which serves up Pacific Rim-inspired plates like bluefin tuna poke and pork belly bao. As island beats play, settle into the bamboo bar with your drink of choice: citrusy and shaken or stirred and spirit-forward.

Hungry for more of Boston? Browse Resy’s latest Boston coverage.

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