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3 weeks agoupdated May 01, 2024

The Long Weekend: A Luxury Guide to Boston

Whether you come for the history or the world-famous lobster rolls, there’s always something new to discover.

By Michelle Gross

Boston’s roots run deep: One of the oldest cities in the US, Boston has a reputation for delivering a small-town feel with big-city energy that has always been a part of the draw here. Now, 250 years after the infamous Boston Tea Party, our luxury guide proves Beantown has never been more abuzz.

Considered one of the most walkable cities in America, Boston has been undergoing a luxury renaissance in recent years, thanks to the arrival of some seriously slick new hotels, a stylish new seaport and a bevy of seasonally inspired fine-dining restaurants, sky-high lounges and rooftop bars. Whether you come for the history, the Red Sox or the world-famous lobster rolls, there’s always something new to see, taste and discover.

[See also: The Best Luxury Hotels in Boston]

What to do in Boston

Follow the red-brick road along the 2.5-mile Freedom Trail, one of the most iconic walking tours in the world. While you connect some of Boston’s most historical sites, you’ll be following in the footsteps of America’s founding fathers as you make your way from Boston Common and Faneuil Hall to Paul Revere’s house and the Bunker Hill monument. You can do this walk on your own, or sign up for the official tour. There’s no shortage of museums to choose from, including the beautiful Isabella Stewart Gardner Museum, which houses some of the world’s most impressive collections of European paintings and artifacts in a Renaissance-style Italian palazzo.

Isabella Gardens
The Isabella Stewart Gardner Museum / ©Shutterstock
Public library
The Boston Public Library / ©Shutterstock

Nestled inside the historic McKim Building of the Boston Public Library, The Courtyard Tea Room is a beautiful setting for afternoon tea and sandwiches. In Boston’s North End, hundreds of Italian restaurants, cafes and pastry shops are always fun places to visit. For a taste of some real local flavor, visit Mike’s Pastry, an old-school, cash-only joint that has earned the title ‘home of the cannoli.’ Word to the wise: Mike’s also has a location in Harvard Square, and they accept credit cards there.

Finally, for some of the best 360-degree views in town, View Boston opened on the top three floors of the Prudential Center in 2023; from the sky-high views to a brand-new bistro and bar, it is a great place to see, sip and savor the skyline from above.

The best hotels in Boston

The Dagny

Set inside the historic Batterymarch Building, The Dagny Boston reopened as an independently owned hotel in 2023. Featuring 377 newly renovated guest rooms and 26 spacious suites, it is the ideal jumping-off point for exploring some of the best sites Beantown has to offer.

There’s a variety of room types, all of which come flooded with natural light and outfitted with modern amenities, floor-to-ceiling marble bathrooms, extremely comfortable beds and delightful Art Deco touches at every turn.

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The handsome ground-floor library and the Tradesman Coffee Shop & Lounge (with its delightful pastries and coffee) add to the overall allure. The real secret weapon is the hotel’s certified Les Clefs d’Or concierges, who provide guests the opportunity to enjoy curated itineraries with personalized, unique-to-Boston experiences — perfect for groups and first-time visitors to the city.

From $299 per night. Contact, +1 877 686 5313,

Four Seasons Hotel Boston

Four Seasons Hotel Boston underwent an extensive refresh in 2023 / ©Four Seasons

Nestled among the stately Victorian brownstones in the Back Bay neighborhood, Four Seasons Hotel Boston has long served as the urban retreat of choice for well-heeled travelers. After doing an extensive refresh in 2023, the hotel debuted a swoon-worthy lobby and porte-cochère area inspired by Boston’s very own public gardens right across the way.

The newly enhanced dining experiences and garden aesthetic carried over to the whimsical new restaurant, Coterie, and elegant Aujourd’hui dining room. The gourmet coffee bar and the lap pool boasting views of the Public Garden and Beacon Hill continue to make this urban oasis one of the most resplendent stays in town.

From $995 per night. Contact +1 617 338 4400,

Raffles Boston

Raffles Boston terrace
The terrace at Raffles Boston / ©Raffles

A hotly anticipated hotel opening in the US last year, Raffles Boston marks the 136-year-old Singaporean brand’s first foray into North America, ushering in a new era of luxury in this gleaming urban oasis with 147 elegantly appointed guest rooms, sumptuous suites and private residences in the fashionable Back Bay neighborhood.

Make your way up to the 17th-story Sky Lobby via rose gold elevators; a world of decadence and your own personal butler await. The hotel features signature dining experiences at its fine-dining restaurant, Amar, as well as all-day dining, afternoon tea service, cocktails and mocktails at The Long Bar. The real pièce de résistance is the Writer’s Lounge, a signature Raffles space made famous for the writers and poets who visited the Raffles hotels over the years.

Back on the fourth floor, a world of wellness awaits at the spa, complete with a 65-ft lap pool, hot tubs and treatment rooms.

From $1,300 per night. Contact Simon Rodrigues, director of sales and marketing, reservations., +1 800 768 9009,

The Ritz-Carlton Boston

The Presidential Suite is the pinnacle of opulence at The Ritz-Carlton, Boston / ©The Ritz-Carlton

Don’t get me wrong, if you’re coming to Boston, chances are you are coming for the city’s history. But even so, sometimes we all need a bit of contemporary luxury and glam. Enter the Ritz-Carlton Boston. Despite its long-standing roots in the city, first arriving in Boston in 1927, a 2001 regeneration saw the hotel transform into the form of a sleek 35-floor tower. 

Found in Downtown Crossing, opposite Boston Common, the hotel serves as an urban oasis, where the caramel-hued marble lobby with moody lighting and an elongated Art Deco bar make for an impressive first impression. Additional hotel features include the Avery Bar, with its signature martinis and mid-century glamour, and the adjoining Equinox Sports Club. 

From $730 per night. Contact +1 617 574 7100

The best restaurants and bars in Boston

When it comes to fine dining, Amar, set on the 17th floor of Raffles Boston, is hands-down the hottest ticket in the city these days. Executive chef George Mendes’s seasonally inspired, seafood-centric menu comes with a modern Portuguese twist. On the same floor, don’t miss Long Bar & Terrace, which offers a mix of light bites and New England classics, with views over Boston’s beautiful skyline. Make sure to order the Boston Sling, which pays homage to Raffles’ most legendary cocktail, complete with homemade apple shrub and Blind Duck Gin.

Cocktails at Raffles
Amar, set on the 17th floor of Raffles Boston / ©Raffles

Of course, no visit to New England would be complete without trying a lobster roll, and Row 34 in the Seaport District stands by its claim to serving the best rolls in town. Meanwhile, Quincy Market near Faneuil Hall offers more than 150 restaurants, shops and vendors. It’s worth the photo opps, and don’t miss the famous clam chowder bread bowl at Boston Chowda Co or a lobster roll combo that comes served with fresh Maine lobster on a warm buttery brioche.

Come game time, beer and baseball lovers flock to Bleacher Bar in Fenway Park, where buckets, bottles and tallboys are the name of the game. Nearby, the Time Out Market is a great place to find a wide variety of some of the city’s top local chefs, restaurants and food trucks pre- or post-game. Before you go, Pinky’s in Back Bay is the place where cocktails and dreams are made. Helmed by executive chef Scott McCarthy, from weekend brunch to light snacks and late-night libations, this sexy new spot off Newbury Street is serving up some of the most Insta-friendly vibes in town.

The best time to go to Boston

Considered the country’s largest Fourth of July event, Boston Harborfest is a celebration of all things Boston. With celebrations taking place all over the city, from fireworks to live concerts and performances, the five-day event in July is a great time to see the city come alive in all of its glory.

Since 1912, baseball fans have flocked to Fenway Park to catch a Red Sox game. The season runs from April through October, and if you’re in town, a game is a can’t-miss. In the off-season, Fenway Park tours run daily November 1 to March 31.

You can’t miss the Duck Boat tour. Considered Boston’s best sightseeing tour, this half-land, half-aquatic adventure is a rite of passage for first-time visitors. For something a little more intimate, Boston Electric Boats offers the chance to be the captain of your boat or to charter a boat for the day and cruise around the harbor.

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