Globe Bar & Cafe

Back Bay

Relocated Boylston Street favorite takes over a beloved, secluded deck
When Poe’s Kitchen at the Rattlesnake closed after a quarter-century, it felt like the end of a rooftop drinking era. After all, what young Bostonian hadn’t slurped back a few G&Ts while lounging atop the alfresco enclave? So take heart: The Globe Bar & Cafe -- previously located up the street -- has taken over the space and left the roofdeck alone, which means you can still duck out of your office early and be drinking an alfresco frozen mudslide before you know it.

Sky Lounge


Proof that small hotel rooms can boast big amenities
This is the very rare roofdeck bird that operates all year round thanks to its indoor space. But the Yotel hotel bar really gets going in summer, with morning meditation (Tuesdays), weekly music performances (Thursdays), and end-of-the-weekend afternoon parties with free-flowing mimosas and spritzes. This on top of a stunning 12th floor terraced view of the water.

Courtesy of the Revere Hotel

Rooftop at Revere

Theatre District

Go for the lobster roll, come back for the weekly specials
There’s a little bit of paradise seven stories above the Theatre District at Revere’s rooftop hideaway. The 16,000-square-foot space got a major makeover in the off-season, with a bigger bar, sleek new furniture, and a new entrance so you don't have to awkwardly walk past the families splashing around in the adjacent indoor-outdoor pool. The elevated menu includes cocktails like the Boston Common Cucumba (Belvedere vodka, lemon juice, simple syrup, fresh cucumber, basil leaf) and snacks like tuna tartare tacos and charcuterie (don't worry, the lobster roll hasn't gone anywhere). New this year: dollar oysters on Mondays, weekly rooftop yoga, and a frozen cocktail menu with brain-freezing beauts like the Frozen Red Bull Vodka. Day passes and cabana rentals are available, but admission is still free after 5pm.

The Colonnade Hotel Rooftop Pool

Back Bay

The city’s only roofdeck, outdoor pool open to the public
The stunning rooftop pool at The Colonnade is like heading to a tropical location without ever leaving Back Bay. Curtained cabanas and wicker lounge chairs line the deck, and Brasserie Jo supplies seasonal cocktails, rotating craft brews, and some light fare for poolside snacking. You’ll have to be a hotel guest or resident to get in on the weekends, but it’s a great spot for a post-work sip ‘n’ dip for the 9-to-5 crowd -- especially those worker bees who appreciate morning rooftop workouts and regular cookouts guest-starring area chefs.

Eric Levin/Envoy Hotel


Fort Point

Jockeying for best roofdeck in the city -- certainly the best views
When this eighth-floor space opened a few years ago, the competition to nab entry was downright fierce. It’s understandable: We're talking Boston Harbor and skyline views, snacks like bacon and roasted corn flatbread, many a refreshing cocktail made with locally produced spirits, and an exclusive-yet-chill vibe. Since then, things have only gotten better: an off-season renovation netted us 2,500 additional square feet and the brand-new Harbor Lounge, a lush VIP area with seating looking out right over the harbor.

The Baseball Tavern


Nothing fancy because it doesn’t have to be
Located roughly a fly ball away from Fenway, Baseball Tavern’s roof deck is the place to be before, during, and after a Sox game, whether or not you have tickets. Overlooking the beloved ballpark, this no-frills watering hole supplies mostly the basics, because you don’t need more than domestic suds and deep-fried apps when you’re scoping these sights.

Chip Nestor

Legal Harborside

Seaport District

About as glam as Greater Boston’s roofdecks get (pretty glam!)
Legal’s flagship by-the-sea goes overboard with its posh indoor/outdoor rooftop lounge and appropriately named Promenade Deck. And it’s under full sail all four seasons thanks to a retractable glass roof and movable walls. Catch the sunset while slurping infinity oysters, and treat your friends to pitchers of punch. Say it with us... ”pitchers.” There’s also a full sushi menu of refreshing bites perfect for summertime feasting.


Harvard Square

Expansive and lovely, yet still undersung Harvard Square roofdeck
Daedalus’ sleek upper deck has plenty of tables, shade, and a fully stocked upstairs bar so you won’t go thirsty. Start your week off or end your weekend right with Sunday brunch (get the stuffed French toast), then stick around for an afternoon fueled by mojitos and seasonal beers. If you’re there long enough to eat again, the Rhode Island–style calamari with fried cherry peppers and chipotle aioli pairs well with any brewski.

Felipe's Taqueria

Felipe’s Taqueria

Harvard Square

Tacos, margs, what more do you need?
Felipe’s christened its roof a few years ago, and it’s been a non-stop fiesta ever since (weather-permitting). With a ton of tables and umbrellas, it’s the perfect place to knock back a margarita or cerveza, chow down on baja tacos, and mock people in the square who wish they were you.


Cleveland Circle

Where BC alums go to mingle outside and up a floor
Keeping watch over Cleveland Circle, Cityside’s cozy roof deck is an urban oasis stocked with shady umbrellas and summery beverages. In addition to a lengthy beer list and six kinds of mules, this spot pours an array of thirst-quenching cocktails, like the John Daly (sweet tea vodka, lemonade, iced tea) and a classic mojito. If rumors of Mary Ann’s imminent demise are true, expect even more BC grads to be elbowing for upstairs space.

Dave Baldwin/Thrillist

Pier 6


The next best thing to your own private harborside veranda
If you’ve never seen Boston and the harbor from Pier 6’s roof deck, then you’re missing out big time. The chic terrace’s seafood-heavy menu includes a raw bar, grilled octopus, and baked crab cakes, and for your summer sipper, indulge in the house Mai Tai made with Gosling’s and Real McCoy rums.

Ristorante Fiore

North End

A roofdeck that’s just one of the many hidden North End gems
From the marble-topped bar to the cast-iron furniture, Fiore’s roof tilts classy-yet-relaxed. For dinner, the grilled Bistecca alla Fiorentina is the way to go, and you’ll find plenty of Italian vino options to accompany it. Post-meal, indulge in top-shelf liqueurs, grappas, ports, and single malts for even more relaxation.



South Boston

Where else do you get to drink outside and upstairs astride an Airstream?
The deck features a retrofitted airstream trailer that's now a fully stocked bar, the very one from which you'll be ordering tropical drinks aplenty. With a 150-person capacity, a diverse noshing menu from the restaurant and the two indoor food trucks, picnic tables to chill at, and lawn games to entertain, this rooftop bar is a perfect al fresco hangout.

The Sinclair

Harvard Square

Upstairs, outdoors pregaming before the concert du noir
The Sinclair has been a neighborhood favorite since it opened its doors in 2013, and the casual/cool roof terrace attracts crowds like moths to the proverbial flame. Take over a high-top (or sink into a low-top, your call) as you partake in its boozy wares, such as the Bulleit-based Renegade Ambassador or the vodka-gin Dreams of Mine. Nationally renowned musicians play almost every night here, so be sure to keep up with the events calendar.