Further proof of Eastie’s ascendancy
Cunard Tavern’s menu made a justified splash when the restaurant debuted in 2017 (gourmet dining in Eastie!), but it was the Top Deck that drove people into a joyful frenzy (an epic roof deck in Eastie!). With gorgeous skyline and water views, a walk-up window bar slinging cocktails and brews on tap, and a snack menu of street food bites, it’s a no-brainer for a nighttime rendezvous or weekend day date (weather and crowds permitting).
The next best thing to Monster seats at Fenway
If you stand on your tiptoes and strain your neck reeeeally far…. OK, so you can’t actually see the baseball action, but you can definitely hear and feel the Fenway feels atop this roof just a Xander Bogaerts’ double away from the ballpark. The 150-seat space has its own bar, so there’s no rushing downstairs to get another round. The flat screen TVs on the back walls let you actually watch the game, although the ever so slight time delay can make for some jarring watching, given the in-real-time cheers right behind you.
Trillium Fort Point
A miniscule brewery that’s morphed into an expansive restaurant
For those in Fort Point who love roof decks but seek a mellower scene, Trillium might be your answer -- but only because 2019 marks its first summer. Otherwise the third floor, 65-person space is likely to be the neighborhood’s newest alfresco hot spot, what with its lounge seating and full bar serving all of Trillium’s latest offerings. And while there may not be water views, there are oysters -- a selection of items from the main restaurant menu are available upstairs as well.
When your favorite deck gets a massive makeover
A good thing just got a lot better. Quincy’s favorite roof bar got a major offseason overhaul -- think 5,000 square feet of alfresco space, an herb and produce garden, apple and pear trees, a sushi bar, and an outdoor kitchen serving roof deck-only dishes. Perhaps the best feature? A louvered roof system that can block out any pesky summer showers. The only hitch: the spot isn’t quite open yet (expect its debut a little later in May).
Relocated Boylston Street favorite takes over a beloved, secluded deck
Rising from the ashes of Poe’s Kitchen at the Rattlesnake, the Globe Bar & Cafe has kept the rooftop good times rolling. Translation: you can still duck out of your office early and be drinking an alfresco frozen mudslide free of traffic noise and pollution; an ample rooftop food menu invites you to make a night of it.
Proof that small hotel rooms can boast big amenities
This is the very rare roofdeck bird that operates all year round thanks to some posh indoor seating. But the Yotel hotel bar really gets going in summer, with outdoor morning meditation on Tuesdays and lots of regular programming throughout the summer (this season’s details are still being worked out). This on top of a stunning 12th floor terraced view of the water and a rotating art display for those rare instances when you grow weary of the scenery.
Where the young and beautiful go to drink, sun, and (literally) look down on the masses
There’s a little bit of paradise seven stories above the Theatre District at Revere’s rooftop hideaway. The 16,000-square-foot space is an elevated oasis of lounge seating, luxe cabanas, shaded swimming, and people-watching that can quickly devolve into gawking. The 2019 summer menus include large-format cocktails, chi-chi frozen drinks, lotsa wines by the glass and bottle, and seasonally inspired snacks (the new menu should be out any day). New this season: the rooftop’s “Wellness Wednesday” power yoga classes at 6:30am. Day passes and cabana rentals are available, but admission is still free after 5pm.
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, all the better to enjoy seasonal cocktails, rotating craft brews, and some light fare for poolside snacking, including pizzas from Regina Pizzeria. 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 weekly morning rooftop yoga workouts. A word to the eager beavers out there: the pool doesn’t open to the public until May 28.
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. We're talking Boston Harbor and skyline views, many a refreshing cocktail made with locally produced spirits (including several large-format cocktails), and an exclusive-yet-chill vibe. Last year’s renovation netted us 2,500 additional square feet and the Harbor Lounge, a lush VIP area with seating looking out right over the harbor. Just remember that it’s drinks only upstairs, so a hop down to the first-floor Outlook Kitchen might be in order at some point.
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, steamed mussels, and baked crab cakes, and for your summer sipper, indulge in the house Mai Tai made with Gosling’s and Real McCoy rums.
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 homemade pastas are the way to go, and you’ll find plenty of Italian vino options to accompany them. Post-meal, indulge in top-shelf liqueurs, grappas, ports, and single malts for even more relaxation.
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 -- the seasonal cocktail list demands multiple visits. Nationally renowned musicians play almost every night, so be sure to keep up with the events calendar.
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.
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.
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.
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.
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.