After Memorial Day, alfresco drinking is pretty much a daily sport. But rooftop bars offer unique pleasures: the views, the (relative) solitude and the high-altitude breezes that break up the most oppressive temperatures. We’ve rounded up the best rooftop bars Boston has to offer, from Back Bay to Harvard Square. So when you need to come out of your Boston dive bar hibernation, this is where you wanna be drinking.
Best rooftop bars in Boston
Kick back in your own private cabana and ask yourself why you ever idealized Miami. The Theater District hotel boasts the scene-iest rooftop scene in the city, an amalgam of chicly dressed waitstaff, equally well-outfitted guests, and a smorgasbord of tropical drinks and low-cal munchies. Lounge on a reserved couch before hitting the mostly glass-enclosed pool, which is open to all bar visitors. The seven-story-high spot offers a beautifully distracting, 270-degree vantage point from which to gaze down upon all those ground-level lesser-thans.
When you want to show the city off to an outsider, you take them to the roof deck at Legal Harborside. The plush lounge seating is a serious upgrade on run-of-the-mill iron patio seats; an impressive wine list and stripped-down food menu provide everything you need (namely, sparkling rosé and oysters); and of course the truly spectacular view of the harbor puts the city’s waterside charms on full display. The long weekend lines only add to the allure (though irksome to regulars).
The newest entry in the city's rooftop scene was a hit from the nanosecond it debuted, and little wonder: the 270-degree skyline and sunset views alone are worth the long wait times at both the elevator and the bar. The expansive, eighth story spot, part of the new Envoy Hotel in the Seaport, places a premium on luxury, from the comfortable lounge seating to the top-shelf cocktails. Bar bites from the Outlook Kitchen downstairs include pulled pork tacos, salumi flatbread, and two different grade A burgers.
You’ll come for the pool and stay for the food and drinks. Ever since the Back Bay hotel revamped its rooftop oasis in 2014, there’s been no better way to cool off during Boston’s still-stressful summer months. Private cabanas cater to the truly indulgent, but you’re more likely to find us at the 12-person bar enjoying a frozen cocktail and swordfish tacos or a lobster rollbetween dips (the pool area is open to non-hotel guests during the week). Work off that last daiquiri the next day with sunrise yoga, held weekly on the pool deck.
What longtime Bostonian hasn’t tossed back a margarita (or six) atop this rooftop standard-bearer? Fenced in from surrounding Back Bay buildings, the enclosed retreat has hosted a diverse after-work crowd for nearly 25 years. With its own full bar and the Southwest-influenced menu from executive chef Brian Poe (who majorly upgraded the joint back in 2009), you have little reason to drink downstairs until December.
It’s easy to forget about the stalwarts, but Daedalus, housed in a former greenhouse on the outskirts of Harvard Square, deserves another look. The roof deck here is serene and spacious, the perfect spot for both after-work drinks and a Sunday hangover brunch. Red umbrellas protect the sun-phobic, while ceiling fans cool down the covered tables; lush flower boxes add a bit of chlorophyll to the mix. A solid beer and cocktail list combined with a relatively calm crowd adds up to a repeat winner.
An oldie but goodie, Fiore’s rooftop bar feels like a European café crossed with a small alfresco sports bar, with wrought-ironseating sidled up next to an exposed-brick bar and flatscreen TVs. Over at the sit-down tables, an enormous wine menu (spring for that $500 Cabernet Sauvignon already!) joins forces with a classically Italian lunch and dinner menu, though a glass of prosecco and a Margherita pizza are all you need to complement the faint sea breezes.
First it was open, then closed, then open again under new ownership. Let’s use our patronage to keep it afloat, if only for the 45-seat roof deck within a homer’s distance of Fenway Park’s right field wall. The reopening has come with a revamped drink menu and half-priced apps from 10pm to 11pm daily. Eleven flatscreens still let you catch the game as you enjoy the signature all-beef hot dog. It can get crowded, but not half as crowded as Yawkey Way before game time.
It’s Fenway Park for the crowd-adverse. A mini-replica of the Green Monster anchors a deck that also includes Adirondack chairs, flatscreens and a tucked-away little bar hidden beneath an overhang. A super-simple menu of apps and sandwiches lets you focus on the beers while fortifying yourself against excess. Canopies for daytime shade give way to glorious views of the nearby Fenway lighting after dark.