3 Days in Boston

Colonial History, Contemporary Art, Fresh Seafood

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View of Boston, Massachusetts skyline looking across Boston Harbor

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 to travel back in time along the Freedom Trail, with stops including Faneuil Hall, Paul Revere’s home, and Boston Common, the first public park in the US. Delve deeper, and you’ll uncover worthwhile contemporary attractions, preppy-chic hotels, and a pioneering 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 cuisines from 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 you can enjoy throughout your journey when you book through AmexTravel.com or the Amex Travel App™.

Calendar

Best Time to Visit

Boston is particularly enjoyable in late spring (May-June) and early fall (September-October), when temperatures are comfortable and the city’s parks and waterfront offer plenty of reasons to spend time outside. Summer brings festivals, outdoor dining, and warm days along the harbor. Fall foliage typically peaks in October, while winter brings cold temperatures, occasional snow, and fewer crowds overall.

Airplane

Getting There

Enjoy savings on select economy tickets with Delta Air Lines on designated domestic flights through Amex Travel™ with Platinum Member Airfares™* when booked through American Express Travel®. Platinum Card and Centurion Members receive reduced fares compared to fares available for other American Express® Card Members through Amex Travel™

Boston Logan Airport (BOS) – 5 miles

North End & Boston's Waterfront

Accommodations

Raffles Boston

The Atlas Hotel

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Place of Interest

ICA Boston

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Eat & Drink

Little Sage

Neptune Oyster

O Ya

Mike's Pastry

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The Freedom Trail & Cambridge

Places of Interest

Step Back into Colonial History

Tour Harvard and MIT

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Eat & Drink

High Street Place

Oleana

Little Donkey

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Art & Shopping

Places of Interest

Isabella Stewart Gardner Museum

Museum of Fine Arts, Boston

Back Bay & Beacon Hill Neighborhoods

South End Shopping District

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Eat & Drink

The Salty Pig

Greystone Cafe, Bakery, and Provisions

Myers + Chang

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Day 1: North End & Boston's Waterfront
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CHECK-IN • MIDDAY

Raffles Boston

Raffles Boston brings the brand’s signature hospitality to Back Bay, with interiors that draw on the city’s history through copper accents, sculptural details, and nods to the neighborhood’s brownstones. Rooms feature hardwood floors, rain showers, and Guerlain bath amenities, and all accommodations include dedicated Raffles Butler service. Spend the afternoon at the Guerlain Spa and indoor pool, then head to Long Bar & Terrace for New England fare and the signature Boston Sling, or La Padrona for modern Italian.

The Atlas Hotel

At the crossroads of Allston and Cambridge, The Atlas Hotel offers a front-row seat to one of Boston’s emerging cultural and innovation districts. Contemporary rooms and suites feature comfortable workspaces, with many looking toward Boston and Harvard Stadium. Downstairs, the Living Room hosts rotating events and neighborhood gatherings, while Ama serves globally inspired dishes throughout the day. For drinks with a view, make your way upstairs to Foxglove Terrace, the hotel’s rooftop bar.

As a Platinum Card® Member, enjoy a complimentary suite of benefits when you book through American Express Travel®.

Fine Hotels + Resorts*

 

  12pm check-in, when available

  Room upgrade upon arrival, when available1

  Daily breakfast for two

  $100 credit to use toward eligible charges2

  Guaranteed 4pm check-out

The Hotel Collection 3,*

 

  12pm check-in, when available

  Room upgrade upon arrival, when available1

  $100 credit to use toward eligible charges2

  4pm late check-out, when available

Platinum Card Members can get up to $300 back in statement credits semi-annually for up to a total of $600 in statement credits per calendar year* on prepaid Fine Hotels + Resorts® or The Hotel Collection3 bookings through American Express Travel when you pay with your Platinum Card®. See hotel credit details.

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EAT & DRINK • DINNER

Meals That Are Worth Seeking Out

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 regularly stretches out the door (neptuneoyster.com). The restaurant remains walk-in only, but devotees will tell you it’s worth it. In addition to raw bar specialties and oysters, Neptune also excels at its famed Maine lobster roll, available hot with butter or cold with mayo, plus seafood-focused daily specials.

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 memorable splurges. The ever-changing progression showcases exquisite seafood and inventive flavor combinations, with each course given its own moment to shine.

Day 2: The Freedom Trail & Cambridge
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EAT & DRINK • DINNER

Sample the Cambridge Food Scene

Tan hands use a fork and knife to cut into a pistachio katmer layered on top of white saffron ice cream and a bed of pomegranate granité.

Oleana

Oleana is beloved for small plates packed with big flavors that reflect the culinary traditions of Turkey and the Eastern Mediterranean. It’s best enjoyed with a group so that you can sample widely among the meze dreamt up by the acclaimed kitchen team. If the weather obliges, grab a table in the charming garden patio.

A bowl of ravioli topped with dollops of sour cream and a drizzle of red pepper butter.

Little Donkey

Two award-winning chefs joined forces to open Little Donkey in Cambridge’s Central Square (littledonkeycambridge.com). The lively restaurant features an ever-changing menu of small plates inspired by cuisines from around the world. Expect everything from crudo and fresh oysters to creative takes on noodles, seafood, and comfort classics.

Day 3: Art & Shopping
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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 (new.gardnermuseum.org). Let yourself be charmed by the statues and greenery of the glass-encased courtyard and saunter through rooms of art by legends like Matisse and Titian. Empty frames are placeholders for paintings stolen in 1990—still one of the most famous unsolved art heists.

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 one of the largest collections of Japanese art outside Japan. The museum also offers accessibility resources and programs for visitors of all ages and abilities (mfa.org).

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

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