Best rooftop bars in Boston
This Theater District hotel boasts one of the liveliest rooftop scenes in the city, with an amalgam of stylishly dressed staff and guests, and a smorgasbord of tropical drinks and shareable munchies. Lounge on a reserved couch or chill by the indoor, glass-enclosed pool and take in the 270-degree views from this seventh-floor perch. Psst: If you’re not down for purchasing a day pass, the rooftop is free and open to all after 5pm.
When you want to show off one of the city’s most dynamic neighborhoods to an outsider, take them to Legal Harborside’s roof deck. The plush lounge seating is a serious upgrade to run-of-the-mill patio seats, and the spectacular harbor views impress. Work your way through the extensive wine list and seafood-focused menu; sparkling rosé and oysters are always a wise choice.
Majestically perched atop the Seaport’s Envoy Hotel, this expansive, eighth-floor spot places a premium on luxurious comfort, with stylish lounge seating and upscale cocktails. The skyline and sunset views alone are worth the inevitable lines. Inside tip: Expect to wait a bit when visiting after work or before a concert at the nearby Blue Hills Bank Pavilion.
Home to one of the city’s most famous rooftop hangouts, this Back Bay hotel has revamped its 12th-floor pool deck numerous times over the years. A mix of hotel guests and local scenesters rub lotion-covered shoulders while cooling off during Boston’s summer months. Private cabanas cater to the truly indulgent, while most patrons head to the bar to order a frozen cocktail alongside swordfish tacos or a lobster roll. Closed to the public on weekends, the rooftop is open to non-hotel guests (for a fee) on weekdays.
Located on a marina in the Navy Yard, Charlestown’s most popular outdoor drinking and dining spot provides intimate views of Old Ironsides. A colorful mix of locals gaze out on to the city's skyline while nibbling on selections from a crowd-pleasing, seafood-heavy menu (e.g. Point Judith calamari, seared scallops). A well-stocked bar is on hand to help patrons imagine they're on the Cape.
Housed in a former greenhouse on the outskirts of Harvard Square, Daedalus has been a longtime favorite of Cantabrigians seeking open-air environs. The roof deck is serene and spacious, a perfect spot for after-work drinks or a hangover-curing brunch. Large umbrellas protect the sun-averse, while ceiling fans cool down the covered tables; flower boxes add a bit of color to the mix. A solid beer and cocktail list combined with a (normally) calm crowd adds up to a dependable standby.
Outfitted with a vintage Airstream trailer-turned-bar on its roof desk, this 3,000-square-foot Southie behemoth packs a youthful crowd onto its rustic picnic tables. An assortment of globally-minded comfort fare and flavorful, straight-from-the-smoker barbecue satiaties the masses, while local craft brews keep the hops-heads happy. When there's a big game, just about everyone ducks inside to follow the action on a pair of 160-inch projector screens.
An old-school haunt in the heart of the North End, Fiore’s rooftop bar feels like a European café crossed with a small sports bar, with wrought-iron seating and an exposed-brick bar. Over at the sit-down tables, an enormous wine list joins forces with a classic Italian menu, though, in our opinion, a glass of prosecco and a margherita pizza are all you need to complement the breezy atmosphere.
Sox fans looking for an old-school, pre- or post-game hangout pack this mainstay's breezy rooftop patio whenever the weather allows. A mini-replica of the Green Monster anchors a deck that also includes Adirondack chairs, flatscreens and a tucked-away bar hidden beneath an overhang. A simple menu of apps and sandwiches—e.g. burgers, wings, chips and salsa—keeps energy levels high. Canopies for daytime shade give way to allow glorious views of Fenway Park after dark.