The Connoisseur’s Guide to Summer in Boston

The summer of 2026 - the 250th anniversary of America's founding - feels like a particularly ideal time to visit Boston, given the key role this city played in our country's origin story. But look a little closer, and you'll see that any summer is a good excuse to visit New England's largest city. Walkable neighborhoods, fantastic shopping and entertainment, a hospitality scene bursting with creativity, a bevy of world-class hotels... This is everything we're excited about right now in Bean Town:

Boston, Massachusetts

Summer's Must-Visit Restaurant

Opened in July 2025, Capri is 7,000 square feet of la dolce vita, spread out across a voluminous interior with red-velvet curtains and chairs and an expansive stone patio with umbrella-shaded booths and a covered bar. It's a see-and-be-seen setting for Italian steakhouse delights like beef carpaccio, hand-rolled rigatoni alla vodka and a 36-ounce Florentine porterhouse. capriboston.com

Note: If you have trouble getting a table, you'll find the next best thing at La Padrona (similar vibes) in the Raffles Hotel.

Boston's Hottest Bar

The Wig Shop is that rarest of cocktail bars - one that delights and surprises, yet never takes itself too seriously. Enter through the unmarked door beside a faux wig-store display (relax, there's no password) to find a groovy lounge with velvet sofas and playful house originals like the Cinemax After Dark made with mango-infused sherry. Stick around for sexy canapes (like lobster-topped buttermilk pancakes) and a traditional absinthe service. wigshopboston.com

Coolest Boutique of the Moment

In recent years, vintage watches and jewelry have made the move from pawn shop merchandise to highly sought-after grails. It's a market sea change seized on by Material Good, which chose a second-story space on the first block of Newbury Street for its third location. Within the airy, art-filled boutique, discerning costumers can examine vintage Pateks and Piguets alongside a curated collection of rare jewelry and in-house creations. materialgood.com

Best Neighborhood for Shopping Like a Local

With its neat rows of 19th century brownstones and pocket-sized parks, the South End looks (and feels) like quintessential Boston. The supremely walkable neighborhood is also home to dozens of independent shops and boutiques, from preppy menswear at Sault New England (saultne.com) to local produce at Siena Farms to natural vino at Neighborhood Wines (neighborhoodwines.com) and much, much more.

Darling

Best Neighborhood for Date Night

There's long been a sense of electricity around Central Square, which has forever catered to students and Bohemians with its record stores and rock clubs. More recently, it's become a bonafide dining and drinking destination for the rest of us. Consider starting the night with a tipple at the inventive, Asian-inflected cocktail lounge Darling (darlingcambridge.com) before continuing to Si Cara (sicarapizza.com) for heavenly canotto-style pies or PAGU (gopagu.com) for an eclectic blend of Japanese and Spanish flavors.

Summer's Must-Attend Theater

The Colonial Theatre, operated today under the auspices of Emerson college, has the distinction of being Boston's oldest continually operating theater. The palatial looks with which it opened in 1900 have been largely preserved, and it's become the home base for touring Broadway shows and celebrities: the 2026 season includes the John C. Reilly musical Mister Romantic, plus an evening with everyone's culinary godmother, Ina Garten. (us.atgtickets.com)

Touristy Things The Locals Actually Love

Neptune Oyster (neptuneoyster.com) in the North End regularly has a line around the block of folks waiting for its famous lobster rolls. And you know what? The cozy restaurant - which earned an overdue Michelin Guide recommendation last year - is totally worth it. Pro-tip: Spring for the caviar-topped johnnycakes. Afterward, go comparison cannoli shopping on Hanover Street with stops at Mike's Pastry (mikespastry.com) and Modern Pastry (modernpastry.com).

The Ultimate Summer Market

Bostonians love their summer markets. And every Sunday from May to Mid-November, the SoWa Open Market (sowaboston.com) draws crowds to the southernmost stretch of the South End for open artist studios, a subterranean vintage mart, food trucks galore and a sprawling outdoor bazaar where the best New England farmers, artisans and small businesses ply their wares. Always a good time.

Where to Stay-Hotel Directory

Boston Harbor Hotel

Few hotels can boast better real estate than the 232-room Boston Harbor Hotel, which makes the most of its waterfront location with an iconic, 60-foot archway that hosts an enormous American flag. Ooh la la: spectacular John Adams Suite presidential suite. $$

Fairmont Copley Plaza Boston

The grand dame of Back Bay, the historic Copley charms with 383 guest rooms, a lavish old-school lobby and the perpetually packed OAK Long Bar + Kitchen on its first floor. $$

Four Seasons Hotel Boston

The elder of two Four Seasons in Boston, the downtown original on Boylston Street reemerged not long ago from a fabulous Wes-Anderson-esque makeover, boasting 239 rooms, an elite health club with 44-foot indoor pool and the French fusion restaurant Coterie. $$$

Four Seasons Hotel One Dalton Street

This 214-room Four Seasons occupies 21 floors of the Back Bay's 61-story One Dalton tower. One of those floors is fully dedicated to its wellness complex, complete with 64-foot heated lap pool. The Charles Suite has one of the city's best private terraces. $$$

The Langham Boston

A five-star, 312-room stunner located in the former Federal Reserve Bank of Boston, the Langham ties back to its London roots with an elevated English-style pub, the Fed. $$$

Mandarin Oriental Boston

Located within the Prudential Center - steps from some of Boston's finest shopping - this 148-room refuge is home to one of the region's best spas. The Back Bay corner suites have swank kitchenettes. $$$$

The Newbury Boston Hotel

Found on the historic intersection of Newbury and Arlington streets - ooh, did someone want to go shopping? - the chic, 286-room Newbury boasts one of the city's best rooftop restaurants, Contessa, from the Major Food Group. $$

The Newbury Boston

Raffles Boston

Every single one of this hotel's 147 rooms comes with round-the-clock butler service. Raffles' 35-story modern tower includes a dramatic, three-story sky lobby that overlooks Copley Square. There's a Guerlain spa - ahhh - and a 66-foot lap pool. The Raffles Suite (aka presidential suite) is simply stunning. $$$

The Whitney Hotel

Nestled at the flat of Beacon Hill between Charles and Cambridge streets, the 65-room Whitney suffuses old-world charm with a modern, boutique hospitality touch, and has become a landmark in its own right. $$

XV Beacon

Situated in a Beaux Arts building at the peak of Beacon Hill, the 61-room XV Beacon sweetens the deal by housing Mooo...., one of Boston's premiere steakhouses and most coveted reservations. Not necessary for summer, but every room has a fireplace. Dogs love this one. $$

This article originally appeared in OLTRE Volume 14 Summer 2026.
Writing: Eric Twardzik
Photography: Marcus Lloyd
Creative Direction: Devin Duckworth
Styling: Abby Brenc @ Anchor Artists
Beauty: Rachael Berkowitz @ Anchor Artists
Modeling: Carlin Phillips @ NEMG, Genevieve Glenn and Chris Hanley @ Maggie
Photo Assistant: Kyle Peters
Styling Assistant: Lauren Gilgan