• Wed. Dec 8th, 2021

Boston Summer 2021 Weekend Travel Guide

ByKeith M. Jones

Jul 30, 2021

William B. PlowmanGetty Images

When a city like Boston has been around since 1630, there are a lot of opinions about what to do there, and let’s be clear, Bostonians have a lot of opinions. So yes, newcomers should definitely hike the Freedom Trail, catch a boat on the St. Charles and stroll through Cambridge to soak up the museums and Harvard buildings. But we like to give a little to our summer trips City Country spinning, like settling down in a caviar-flowing restaurant (Saltie Girl), grabbing Virgil Abloh’s very first museum exhibit (and picking up the limited-edition loot that goes with it), or restocking your company wardrobe Boston’s not-so-secret closet (Alan Bilzerian). Below are the very T&C things to eat, do, shop, and see in Boston this summer.

Where to stay

The Envoy Hotel

Boston’s summers can get hot and humid, so insiders know it’s time to escape to the Seaport District, which has a constant, refreshing breeze on the water. The Envoy’s modern rooms overlook Boston’s waterfront, and the rooftop bar is a hot spot on the weekends. The easy walking distance to amenities like Equinox and La Colombe makes it an ideal choice for people who like to maintain their daily routine on vacation while still feeling immersed in the city.

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Where to eat

Bakery & Café Tatte

Bostonians are obsessed with this Israeli-inspired coffeehouse chain – get the shakshuka and an almond croissant and you’ll see why.

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Chopped off

The Italian-American culture in Boston is lively and in your face in the best way, but if you’ve ever strolled around the North End (and ideally grabbed a cannoli from Mike) then head to this South End enoteca for it. A relaxed Italian atmosphere that goes so well with a long day of travel.

Oh yes

This omakase sushi experience is located in a century-old fire station in Boston’s Historic Leather District and has bragging rights everywhere, not least because the sashimi, nigiri, and sake live up to the hype.

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Saltie girl

Among Boston’s many culinary odes to seafood, cult favorite Saltie Girl is a staple. Start with the canned fish and clam chowder, don’t skip the lobster roll, and yes, you should buy extra bags of sea salt and vinegar chips for later.

What to do

Virgil Abloh: Figures of Speech at the Institute of Contemporary Art

Don’t miss the first museum exhibition on the artistic director of Louis Vuitton and founder of Off-White, Figures of speech covers Abloh’s artistic work, spanning album covers and illustrations right down to his best-known fashions. Abloh has also worked with area students, promoting diversity and creativity across Boston as part of his creative mission to change the status quo from within. There is also a “Church & State” pop-up store to purchase limited edition pieces designed by Abloh himself.

virgil abloh exhibition
Virgil Abloh’s very first museum exhibit is at the ICA in Boston until September.

Courtesy of ICA Boston

Isabella Stewart Gardner Museum

The star of the Netflix docuseries, It’s a robbery: the biggest art heist in the world, and the beloved Boston institution is worth a visit in any season. This summer, the Titian room, which features Titian European rape is being restored while the painting is on display at the Prado Museum. It returns to the Gardner in August, but take an in-depth look at the room’s meticulous renovation (and a close-up of the Prelle wall coverings to die for) if you go before.

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Fenway Park

It’s not on the list for athletes. Athletes already know they should go to Fenway Park and have probably barked about the “Green Monstah” for weeks before this trip. For those who have little interest in the great American hobby, you should still go. The stadium has a lot of vintage charm that makes it easy to understand “why baseball”. Kiss the bottom of your high-low mix with a hot dog and a beer and we promise you will have a good time – just for god’s sake, don’t wear anything that can even look like Yankees’ colors because some people really, you know, to do baseball over here.

New York Yankees vs. Boston Red Sox
Fenway Park, an institution for baseball fans … and the rest of us.

Billie Weiss / Boston Red SoxGetty Images

Boston Pop Orchestra

Even pop music has been around in Boston since 1900. The Boston Pops Orchestra (an offshoot of the Boston Symphony Orchestra) hosts several shows throughout the year with lighter, more contemporary music. This summer, John Williams movie night is Friday August 13th.

Where to shop

Brattle Bookstore

Founded in 1825 and located near Boston Common, this bibliophile’s paradise has three floors filled with books. Go directly to the third floor, where the rarest and most valuable tomes are kept.

boston brattle bookstore
Boston’s Brattle Bookstore has been an institution for centuries.

Karen kasmauskiGetty Images

Alan bilzerian

Alan Bilzerian is a glorious refuge from a bygone era when some shop owners ruled the sartorial world (think Jeffrey from New York). Not only is it stocked with Pleats Please by Issey Miyake, Rick Owens, Ann Demeulemeester and others, but its own private label is made in-house and is full of high basics that are definitely worth revamping your suitcase to take home a new one. Bostonian approved wardrobe.

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