Here's Our Travel Guide to This Nation of Over 7,000 Islands
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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 tartar tacos and charcuterie (don't worry, the lobster roll hasn't gone anywhere). Day passes and cabana rentals are available, but admission is still free after 5pm.
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.
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. Reservations are recommended.
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.
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.
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, coconut Mai Tais, 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 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.
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 five kinds of martinis, this spot pours an array of thirst-quenching cocktails, like the John Daly (sweet tea vodka, lemonade, iced tea) and the Cleveland Circle Collins (Tito’s vodka, muddled raspberries, lime juice, simple syrup).
Floating casually between office buildings, Market’s roof deck puts you sky high in the FiDi for cold beers, appetizers, and after-work good times. In the cold-beer category, domestic cans and Harpoon Big Squeeze drafts will quench your mighty thirst, while fried dill pickles and a pomme frites trio will satisfy your munchies. As for those good times, check out Industry Night Wednesdays from 9pm to midnight for $3 drafts, $5 wines, $6 drinks, and half-price apps.
South Beach comes to Newton at BOKX 109’s rooftop pool, with enough cabanas and day beds for an army of sun worshippers. With savory burgers and a rotating list of creative cocktails, the emphasis here is on fun. It’s closed to the public on Saturdays, but otherwise, passes run from $30 ($25 for Newton residents) up to the four-cabana fire pit rental, which comes with a $12,000 food and beverage minimum.
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 lamb lollipops, and for your summer sipper, indulge in the house Mai Tai made with Gosling’s and Real McCoy rums.
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.
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 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.