3 Days in Boston

Colonial History, Contemporary Art, and Fresh Seafood

by American Express Travel®

|

September 12, 2025

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

by American Express Travel®

September 12, 2025

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

The Newbury Boston

Map
Place of Interest

ICA Boston

Map
Eat & Drink

Woods Hill Pier 4

Neptune Oyster

O Ya

Mike's Pastry

Map

The Freedom Trail & Cambridge

Place of Interest

Step Back into Colonial History

Tour Harvard and MIT

Map
Eat & Drink

High Street Place

Oleana

Little Donkey

Map

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

Map
Eat & Drink

Saltie Girl

Greystone Cafe, Bakery, and Provisions

Myers + Chang

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

The Langham, Boston

The Langham, Boston

Located in the Financial District on Franklin Street The Langham, Boston occupies a designated landmark—the original Federal Reserve Bank of Boston—and complimentary guided Heritage Tours delve into the building’s past. But it’s also kept up with the times. The Langham reopened in 2021 after a two-year makeover that introduced a new club lounge and refreshed the gorgeous 312 rooms and 17 suites, now with marble baths with walk-in showers. The flagship Italian restaurant Grana is a stunning space with sparkling chandeliers while The Fed is a more casual option for craft cocktails and British pub food. There’s also a heated indoor pool, a spa, and a fitness center with Technogym equipment and Peloton bikes.

In the lobby of the Whitney, a blue velvet couch faces two gray armchairs next to a roaring fireplace, all in front of a bronze elevator.

The Whitney

The Whitney

This red-brick boutique hotel blends in with the townhomes of the Beacon Hill neighborhood and welcomes guests into a living room-like lobby with a fireplace and cabinets full of books by Massachusetts authors. Pets will also feel at home, thanks to complimentary plush dog beds and bakery treats. Many of The Whitney’s 65 refined rooms and suites overlook the nearby Charles River. Explore by sailboat rental or on a complimentary bike—just be back in time for a dinner of hake and wild mussels at the coastal Italian restaurant Peregrine.

Mandarin Oriental, Boston

Mandarin Oriental, Boston

Situated on Boylston Street in the historic Back Bay neighborhood, Mandarin Oriental, Boston offers direct access to the Prudential Center and the shops of Copley Place. The lobby feels like a calm oasis and the exceptionally spacious rooms combine classic New England elegance with refined Asian touches. Visit Bar Boulud for fresh oysters, the Lobby Lounge for afternoon tea service, and the airy spa for some serious relaxation.

The Newbury Boston

The Newbury Boston

Built in 1927, The Newbury Boston originally opened as America's very first Ritz-Carlton. Today, it blends historic gravitas with all the trappings of contemporary luxury. Overlooking the Boston Public Garden, the hotel puts you steps away from Back Bay’s best, from monuments to cultural landmarks, all of it within strolling distance of Newbury Street’s brownstone-front boutiques. On-site, Contessa serves northern Italian fare with a view, The Street Bar offers elevated cocktails, and the Library Lounge lets you unwind in quiet, exclusive comfort.

Platinum Card® Members have access to the following benefits with Fine Hotels + Resorts® and The Hotel Collection bookings 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 towards eligible charges2

  Guaranteed 4pm check-out

1Certain room categories are not eligible for upgrade.
2Eligible charges vary by property.

The Hotel Collection *,3

 

  12pm check-in, when available

  Room upgrade upon arrival, when available1

  $100 credit to use towards eligible charges2

  Late check-out, when available

1Certain room categories are not eligible for upgrade.
2Eligible charges vary by property.
3The Hotel Collection requires a two-night minimum stay.

2
EAT & DRINK • LUNCH

Enjoy a Spectacular Lunch in the North End

Overhead view of a salad in a white dish on a teal wooden table. The salad includes dark greens, wedges of hard-boiled egg, and salmon.

Woods Hill Pier 4

If Boston had a Michelin Guide, Woods Hill Pier 4 would surely make the cut. This restaurant prepares exquisite farm-to-table cuisine that is sustainable, seasonal, and rich in flavor and nutrients. Start your meal with fresh seafood from the raw bar and carry on with homemade pastas and succulent meats like grass-fed ribeye and pork shoulder—all while taking in the harbor view.

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3
PLACE OF INTEREST • AFTERNOON

Take in Contemporary Art on the Waterfront

Exterior view of the Institute of Contemporary Art, with a large translucent top floor hanging over two smaller glass-walled floors.

ICA Boston

The harborside Institute of Contemporary Art is one of America’s leading contemporary art and cultural venues. It stands out for a permanent collection with numerous works by leading female artists, among them, Louise Bourgeois, Eva Hesse, and Kara Walker. Make the most of your visit by joining a free guided walk, gallery talk, or workshop—and swing by the gift shop for delightful and design-forward products. In summer, you can catch ICA’s water shuttle to explore the seasonal ICA Watershed across the harbor (icawatershed.org).

Purchase ICA Boston tickets online.

4
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 (neptuneoyster.com).  “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 (o-ya.restaurant). The exquisite, flavor-packed dishes arrive one by one so that each gets its moment to be savored and appreciated.

5
EAT & DRINK • DESSERT

Mike’s Pastry

Close-up view of a pistachio cannoli propped up on a plain cannoli, with a chocolate cannoli just behind.

Mike’s Pastry is a non-negotiable stop when in the North End of Boston (mikespastry.com). Since 1946 it has been selling a wide variety of pastries, but cannoli are the specialty. Flavors range from original to mint chocolate chip to limoncello. They only accept cash, and the line is usually out the door.

Day 2: The Freedom Trail & Cambridge
1
SELF EXPLORE • MORNING

Step Back into Colonial History

Statue of George Washington atop a horse in the lush Boston Public Garden, near the Boston Common and the start of the Freedom Trail.

Retrace important milestones from about 250 years ago along The Freedom Trail, a 2.5-mile pathway marked by red bricks that goes from Boston Common to Bunker Hill. Rightfully one of the most popular activities in Boston, The Trail takes anywhere from one to three hours, depending how many of the 16 landmarks you stop to visit. They include Paul Revere’s home and Old North Church where the “One, if by land, and two, if by sea,” signal was sent. Explore more highlights below.

The oldest public park in the United States, Boston Common served as an encampment for British troops during the Revolutionary War and a pasture for cattle until the 1830s. Nowadays, the Frog Pond attracts ice skaters in winter, while theater lovers turn up in summer for Shakespeare on the Common. Year round, activities in Boston Common include picnicking, people-watching, and strolling through this 50-acre green space, crisscrossed by trails and dotted with monuments.

Samuel Adams and Paul Revere helped lay the cornerstone of this Palladian-style building, which was designed by renowned local architect Charles Bulfinch and completed in 1798. Take a tour to learn about the historic paintings and artifacts inside.

John Winthrop, Massachusetts’s first governor, and Mayflower passenger Mary Chilton are buried at Boston’s oldest cemetery, the 1630-era King’s Chapel Burying Ground. From there, walk a few minutes to another 17th-century resting place, Granary Burying Ground, where early patriots like John Hancock and Samuel Adams reside.

A significant building in America’s colonial history, the Old South Meeting House is where debates heated up over Britain’s controversial tea tax—eventually leading to the Boston Tea Party in 1773. Exhibitions pay tribute to that turbulent moment in time.

The Old State House has withstood massacres, revolutionary battles, and fire. Explore every room on a fun, interactive walkthrough that includes art pieces and essential artifacts dating back to the early 1700s.

At the intersection of State and Congress Streets, the Boston Massacre marker is a cobblestone ring that commemorates the 1770 deaths of five civilians during an uprising against British rule.

Faneuil Hall opened in 1742 with market stalls on the ground floor and meeting space upstairs that was used by revolutionary leaders as well abolitionists, women’s suffragists, and labor unionists. A gilded grasshopper-shaped weathervane makes this one of Boston’s most recognizable landmarks. It’s also the site of Faneuil Hall Marketplace, where you can refuel and catch street performers.

This North End cemetery is where many merchants, builders, preachers, and craftspeople were buried, including Robert Newman (believed to have hung the lanterns for Paul Revere) and Edmund Hartt (builder of the USS Constitution). It’s also notable as the final resting place of many enslaved and free African Americans.

Docked at the end of the Freedom Trail, the USS Constitution, built in 1797, is the oldest active ship in the US Navy. It’s free to climb aboard and explore Old Ironsides, a nickname earned during the War of 1812 after a battle in which she helped the Navy capture and defeat five British warships.

This large, granite obelisk was built between 1827 and 1843 to commemorate its namesake: the Battle of Bunker Hill between American Patriots and the British in June 1775. Get schooled on the early confrontation’s significance at the nearby Bunker Hill Museum.
2
EAT & DRINK • LUNCH

High Street Place

Exterior view of High Street Place, its name in a retro gold font over the door, and tables of diners filling the patio under heat lamps.

High Street Place, a vibrant food hall that celebrates local diversity (highstreetplace.com). Many of the vendors are female and/or people of color and their offerings range from globally inspired street food to artisanal desserts and craft cocktails. High Street Place also hosts cooking demonstrations, live music, and other events.

3
EXPERIENCE • AFTERNOON

Tour Harvard and MIT

Pop quiz: where can you find Boston’s most exquisite collection of glass flowers? At the under-the-radar Harvard Museum of Natural History (hmnh.harvard.edu). It’s just one example of why you don’t need to be a prospective student or parent to appreciate a campus visit. For insights, book a guided tour that combines Harvard and MIT (boshist.org); stops include Winthrop Park, the Red House, and The Old Well Brattle House. Leave time to explore Cambridge, which has become a hub not only for higher learning but also for some of the Boston area’s buzziest restaurants.

4
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 in a group so that you can sample widely among the meze dreamt up by James Beard Award-winning chef Ana Sortun. If the weather obliges, you can dine out in the garden.

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

Little Donkey

Two James Beard Award-winning chefs joined forces to open Little Donkey in Cambridge’s Central Square (littledonkeycambridge.com). This collaboration has a menu of small tapas plates inspired by dishes from around the world, like the Wok Fried Chow Fun, Cacio E Pepe and Chili Beef Stroganoff. A meal here is a journey through diverse flavors.

Day 3: Art & Baseball
1
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.

2
EXPERIENCE • LATE MORNING

Fenway Park Tour

The facade of Fenway Park is red brick with tan accents. Flags along the side list the years of Red Sox AL pennants in red, white, and blue.

Since 1912, fans have poured into Fenway Park to root for the home team right in the heart of Boston. It is the oldest Major League Baseball stadium in continual use and the only one that still features a hand-operated scoreboard. Guides lead you through the hallowed walls and out on to the field itself, as they share legendary moments of Fenway Park and bring its history to life with vivid anecdotes. You can also enjoy the views from the Green Monster, a wall that overlooks left field and measures 37 feet and 2 inches tall.

Book the Guided Fenway Park Tour via GetYourGuide.

3
EAT & DRINK • LUNCH

Saltie Girl

A charcuterie board is arrayed with lemons, herbs, dips, bread, and cans of tinned fish. Close-up view of a toasted lobster roll glistening with sauce on a white plate, accompanied by a wedge of lemon and a pile of potato chips.

This tiny 6-booth and counter seating restaurant in Back Bay has an amazing seafood menu. Dive into dishes like fried lobster and waffles, French burgundy snails, whole belly Ipswich clams, or hearty clam chowder. Don’t pass up a charcuterie plate of tender little bites of tinned fish.

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4
SELF-EXPLORE • EARLY AFTERNOON

Boston's Back Bay & Beacon Hill Neighborhoods

View down Acorn Street, a narrow passage with cobblestoned streets, red brick houses, and climbing ivy, and bright green window planters.

Below are some of our favorite spots to hit in the attractive neighborhoods of Back Bay and Beacon Hill, full of landmarks, restaurants, and green spaces.

It feels tranquil and inspiring inside the Renaissance Revival halls of the Boston Public Library’s flagship location, which is also our nation’s first public library. Tours shed light on its significance and highlights like murals by John Singer Sargent. The onsite café is a hidden jewel, where you can linger over afternoon tea (bpl.org).

One of the sweetest activities in Boston is paying a stop at this shop and café off Newbury Street for chocolates made from responsibly sourced cocoa beans without additives. Chocolate is also on the menu, along with premium coffee and tea options. Boxes of the award-winning animal-shaped chocolates make satisfying souvenirs (burdickchocolate.com).

Established in 1837, the Public Garden was the first public botanical garden in America. It encourages embracing old-time pleasures like a long wander along the water or a cruise on the lagoon in one of the famous swan boats.

Great minds have gathered here to learn and exchange ideas since 1807. Indeed, the membership-driven library is a who’s-who of Massachusetts luminaries, such as Ralph Waldo Emerson, Louisa May Alcott, John Quincy Adams, and John F. Kennedy. The building comprises an extensive collection of rare books, thousands of paintings, drawings and artifacts, and a public gallery.
5
EAT & DRINK • AFTERNOON TREAT

Greystone Cafe, Bakery, and Provisions

Through the walk-up window of the cafe, two white women stand arm in arm smiling. Just outside the window, a menu hangs on a brick wall. Overhead view of a tray of chocolate chip cookies sprinkled with chunky salt.

Mother-and-daughter duo Patty and Jacqueline named the bakery after the street on which the pair grew up, and Greystone has a homey vibe (greystonecafe.com). There are patio tables and benches where you can savor your pastries in the sun, plus a walk-up window perfect for taking a treat to go.

6
SELF-EXPLORE

Browse Boston's South End Shopping District

Aerial view of the skyscrapers of Boston’s South End, lit up and reflecting the golden sunset as the day ends.

South End is an artsy and super-chic neighborhood with beautiful Victorian architecture and many boutiques and art galleries. It’s also a hub for Boston’s LGBTQIA+ community.

Amsterdam-born Natalie van Dijk has been introducing Boston to talented furniture and accessory designers since opening Lekker Home in 2003. It’s a destination for those creating a home from scratch as well as shoppers in search of a statement piece or a hostess gift. You might pick up a cozy throw, quirky candleholder, or serving dish to treasure (lekkerhome.com).

Patch NYC was founded by Don Carney and John Ross after they bonded over their love of the handmade process and vintage items. Both designers have spent their whole lives creating and crafting—and, along the way, developed an eye for selecting distinctive home décor and fashion pieces (patchnyc.com).

Michele Mercaldo is a master craftswoman who has created intricate works by hand for over thirty years. Her boutique sells her clean and minimal metal-based handcrafted creations along with those of like-minded jewelers, many of them local. As you shop, you can catch a glimpse of her workstation and take in a gallery space that showcases Boston artists (michelemercaldojewelry.com).

7
EAT & DRINK • DINNER

Myers + Chang

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.

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.

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View from the second seat in a yellow kayak of a woman in yellow paddling. Nearby, two people in a red kayak paddle between cliff faces.

Get more out of your Boston getaway with American Express

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