The NYLON Guide To Boston

What to do, what to eat, where to shop

by Laura Itzkowitz

I have a confession. When people ask me where I’m from, I usually tell them I grew up in Boston but felt like a New Yorker living in exile. I always loved the quaint historic streets and liberal intellectual outlook, but in some ways, Boston felt provincial and preppy, full of people wearing Red Sox caps and polos or awkward nerds I went to high school with. But now that more than 10 years have passed since I moved away, the city seems different—more savvy and cosmopolitan. Those so-called nerds are on their way to curing cancer or engineering robots. Innovative chefs are opening hip new restaurants and bars. Entire neighborhoods are changing, in some cases literally springing up where before there were vast expanses of empty parking lots.

Of course, you can still find the old Boston of Paul Revere and the Founding Fathers. Historic enclaves like Beacon Hill and the North End retain their charm, and the Boston Tea Party is a nice reminder that the city has always had a rebellious streak. But while in the past, glass-walled skyscrapers like the John Hancock Building and the Prudential Center seemed at odds with the stately brownstones of the Back Bay, the city now seems keener to integrate the past with the present. Wander around Fort Point, and you’ll find contemporary art galleries and boutiques in redeveloped warehouses and factories. You can sleep in a former jail reborn as a swanky hotel and dine in a century-old restaurant revamped for the Instagram age. We’ve compiled this handy guide to help you find the best of the new Boston and some of the old.

Photograph courtesy of The Envoy Hotel.

Where to Stay The Liberty Hotel: It used to be a punishment to sleep here, but now visitors to Beantown pay top dollar for the privilege of staying in the former Charles Street Jail, a member of the Luxury Collection. The hotel’s design incorporates cheeky references to its notorious past, including the original catwalks overlooking the lobby and mug shots of celebs like Lindsey Lohan adorning the bar. Unlike the inmates, you can actually appreciate the prime location in Beacon Hill. 

The Envoy Hotel: Opened a couple of years ago, the Envoy—a member of Marriott’s Autograph Collection—brought sleek style and a perfectly positioned rooftop bar to the rapidly developing Seaport. Rooms and suites feature high-tech touches, Netflix streaming, and quirky décor, like TVs perched on bicycle wheels and maps of Boston etched onto glass room dividers.

Verb: This also relatively new hotel is located right by Boston's iconic Fenway Park. Inspired in equal parts by rock 'n' roll music scene and Palm Springs of decades past, this quirky sleeper features an outdoor pool, in-room record players, and retro music posters and album art decor adorning the walls. Attached you'll also find Hojoko, an Izakaya-style restaurant that serves late-night ramen and Japanese-inspired tiki drinks, which, I don't know about you, but, for me, is a major draw to stay here. Irina Grechko

Nine Zero: In addition to offering some of the best views of the Boston Common park and gold-domed Boston State House, this boutique hotel played host to celebrities like Lady Gaga. We love it for its health-oriented amenities like free bikes, yoga mats in every room, and in-room spa services that range from a calming massage to body treatments. —IG

Photograph via Instagram/rukarestobar.

Where to Eat

Ruka: Boston’s new (and perhaps only) Peruvian-Asian restaurant is a fun, modern take on Nikkei and Chifa fusion cuisine inspired by the culinary traditions of Japanese and Chinese immigrants living in Peru. With a mural that looks like a street art version of a Hokusai painting as the backdrop, you can sample Pisco cocktails, ceviche, sashimi, and other specialties.

Tatte Bakery & Café: This charming European-style bakery has locations in Beacon Hill, Harvard Square, Kendall Square, and Brookline, making it a go-to spot for an afternoon pick-me-up or casual brunch no matter where you happen to be. You can’t go wrong with any of their tartines, croissants, and pastries, but I especially love the nut boxes—hard pastry shells filled with pecans or pistachios.

Coppa: Anything that James Beard Award-winning chefs Ken Oringer and Jamie Bissonnette touch, turns to gold, but this casual Italian neighborhood outpost is a standout for its masterfully created charcuterie and cheese plates, housemade pastas and pizzas, and killer appetizers like uni panino and arancini di fontal. Take advantage of the outdoor patio during the summer months.—IG

Toro: Prepare to wait for a table at this very good Spanish tapas restaurant located in Boston's recently revitalized and now hip South End neighborhood—the Maíz Asado, grilled corn with aioli, lime, and aged cheese, is worth the wait alone. Plus, you can leave your phone number and walk across the street to Stella, where you can pass time by ordering an expertly crafted negroni at the bar.—IG

B&G: You can't go to Boston and not go to one of the legendary Barbara Lynch's restaurants. This one continues to remain a favorite for its laid-back approach to New England seafood classics and a wide selection of oysters, which you can also learn to shuck on the premises.—IG

Parish Cafe and Bar: If you haven't yet caught on, Boston has many prominent chefs. If you have time (and money) to visit all of their restaurants, more power to you (also, can we be friends?). If not, head to this sandwich and cocktail joint on Newbury Street that touts creations from a number of award-winning chefs like Bissonnette, Tim Cushman, and Jason Bond. The outdoor patio is great for people-watching.—IG

North End: While Italian neighborhoods in certain cities may only serve to lure in tourists, Boston's North End is the real deal. You will find old Italian men playing dominos on the streets, coffee shops that get packed to the brim during heated soccer matches, and some of the best Italian food around. While Giacomo's is where some will tell you to go for the best bowl of seafood pasta, opt for the less crowded but very good Al Dente located on the street parallel to the popular Hanover Street. But don't skip Giacomo's altogether—just visit its lesser-known Back Bay location that is considerably easier to get into. Also, don't go to the overhyped Mike's Pastry for cannolis like some will tell you—Modern Pastry, across the street, is the way to go.—IG

J.P. Licks: Speaking of dessert, try Boston's very own J.P.Licks. Be warned: The coffee-Oreo frozen yogurt flavor will ruin any other ice cream for you.—IG

Photograph courtesy of Yvonne's.

Where to Drink

Yvonne’s: An evening at Yvonne’s, RUKA's older sister restaurant, feels a bit like a party at an aristocrat’s mansion commandeered by Taylor Swift’s entourage. An antique carved mahogany bar and other original architectural details from the space’s former incarnation as Locke Ober lend the space some gravitas, while contemporary touches like a portrait of Bill Murray in military regalia add a touch of playfulness. 

The Hawthorne: For serious cocktails in a cozy lounge off the Commonwealth Hotel near Fenway, the Hawthorne has long been a leader in Boston’s cocktail scene. Ditch the menu and ask one of the expert bartenders to surprise you with a concoction made with Bully Boy’s small-batch rum distilled in South Boston.

Drink: Brought to you by the Lynch empire, this bar, in the former warehouse district, serves some of the best craft cocktails in the area. It masks as a speakeasy so don't be surprised when you essentially walk into a basement. Also, there is no cocktail menu—rather, you tell your bartender what you like and they tailor-make the libation for you.—IG

Eastern Standard: This is where the industry people go for to get a nightcap—and for good reason. The constantly rotating season sips are always a delightful surprise you didn't know you needed and new takes on the classics will make you forget what the classic tasted like in the first place.—IG

Blue DragonIf you're in the mood for a tiki drink, make your way to this at-first-glance-unassuming Asian gastropub from celebrity chef Ming Tsai that boasts an entire menu dedicated to these tropical cocktails and shareable bowls.—IG

Photograph via Facebook/ICA.Boston.

What to Do

ICA Boston: Long before the Seaport became a destination neighborhood, the Institute of Contemporary Art drew Bostonians to the long-forlorn waterfront. The starkly modern building cantilevers over the harbor, so from inside it feels like you’re floating above the water. Exhibits showcase emerging and established contemporary artists, while the permanent collection has a strong emphasis on women artists, with work by Cindy Sherman, Louise Bourgeois, Nan Goldin, Francesca Woodman, and others. 

Stroll through Beacon Hill: Boston is chock-full of historic churches, cemeteries, taverns, and other sites along the Freedom Trail, but, to avoid the tourist crowds, get off the beaten path in Beacon Hill’s cobblestoned streets. The charming neighborhood lined with brick townhouses extends from Boston Common to Cambridge Street and from the State House to the Charles River. The narrow alleys are Instagram candy, and you can duck into cute boutiques along Charles Street. Once you work up an appetite, make sure to stop by the Paramount, a neighborhood joint marked by some of the best blueberry pancakes you will have and long lines in the morning and afternoon.

Isabella Stewart Gardner Museum: One of my favorite museums in Boston—and possibly the world—is this Venetian-style palazzo built by the Gilded Age heiress and art collector Isabella Stewart Gardner. She must have been a strong independent woman because she was competing with the likes of J.P. Morgan to build the best collection of European Renaissance art in America and supported contemporary artists like John Singer Sargent. A modern glass wing by Renzo Piano was added in 2012, increasing the exhibition space and adding a concert hall, library lounge, shop, and café. 

Harpoon BreweryBostonians love beer, and if you do too, hop over to Harpoon—one of Beantown’s original craft breweries—for a tour on a weekend, and you’ll be surrounded by locals. Tip: Go early to buy same-day tickets. Also, at the end of the tour, you’ll get to taste a variety of brews.

Photograph via Facebook/SoWaBoston.

Where to Shop

Newbury Street: Boston’s version of Fifth Avenue, the two-mile street running through the Back Bay has everything from Chanel to Newbury Comics. The shops are significantly fancier near Boston Common, but if you walk west toward Boston University, the offerings become more affordable. Check out local favorites Trident Booksellers & Cafe for the latest releases, magazines, and giant cups of lattes and Newbury Comics for—you guessed it—comic books, vinyl, and gag gifts. 

SoWa Art + Design District: For work by local artists and craftsmen, look no further than SoWa—a cluster of revitalized warehouses in the South End that’s been transformed into galleries, design showrooms, boutiques, and restaurants. The area is especially vibrant on weekends from April through the end of October for SoWa Open Market, when it’s taken over by food trucks, farm stands, and artisans selling jewelry, clothes, ceramics, and more.