The best rooftop restaurants and bars in Boston

Perched atop the popular Envoy Hotel, this expansive, eighth-floor eatery and bar places an emphasis on luxurious comfort, with stylish lounge seating and upscale cocktails. Come for the skyline and sunset views over the Fort Point Channel, and stay for the Seaport Sangria. Pro tip: Go big and reserve the firepit table.

Hovering above the Theater District and Back Bay, this hotel hotspot is one of the liveliest rooftop scenes in the city. Whether you’re there to crash in your own cabana, stretch out on a couch or chill by the indoor pool, you’ll be able to enjoy the spectacular views in all of their 270-degree glory. It’s one of the most sought-after refuges in town, so be sure to reserve a spot beforehand—and don’t forget to order the special ice cream sandwich of the day.

Located atop The Newbury Boston, this elegant eatery serves more than just comforting Northern Italian fare—it also serves looks in a major way. The inside of this glass-enclosed, rooftop sanctuary seems like it’s a lush garden patio situated on a Tuscan hillside. But if you’re able to pry your eyes away from the beautiful interior for a minute, you’ll also see that this restaurant offers unreal views of the surrounding Back Bay. Take a seat on one of Contessa’s plush chairs, order yourself a selection of salumi and a plate of fresh pasta, and raise your negroni to the cityscape before you. 

The Lifted Pool Bar at The Omni Hotel Boston brings easy breezy city vibes to The Seaport with its rooftop digs and poolside refreshments. Grab a seat at this open-air restaurant and bar, which is located on the fifth floor of this luxury hotel, and enjoy sips, snacks and maybe some swimming as you admire the bustling Innovation District below. The internationally inspired menu ranges from light bites—like citrusy roasted olives—to more substantial plates made for sharing (or solo eating, if you’ve worked up an appetite doing laps), such as a 1-lb salted caramel lobster roll. Wash everything—high-rise vistas included— with an icy beverage from its extensive selection of frozen drinks.

As if Central Square couldn’t get any more hip, along comes Blue Owl and its casually cool rooftop perched atop 907 Main. Overlooking the colorful streets of Cambridge, this chic and sleek spot offers snacks, small plates, skewers, sandwiches and sweets, and features street food favorites from around the world. Savory standouts include a Jamaican oxtail beef patty served with Caribbean slaw and pickapeppa aioli, a podrao Brazilian-style hot dog and lamb kofte kebab. Innovative cocktails should not be missed (our personal favorite is the Dill or No Dill, an unlikely balanced blend of aquavit, peppercorn sochu, dill, cantaloupe and lemon).

Located on the outskirts of Harvard Square, Daedalus has long been a Cambridge staple when it comes to drinking en plein air. The roofdeck of this former greenhouse resembles a secret urban garden with its overflowing flower boxes, oversized umbrellas and the soft glow of stringed white lights. With a menu of elevated wholesome fare and list of classic cocktails, it’s the perfect place to temporarily escape the city’s chaos.

Dorchester Brewing’s rooftop echoes the New England spirit because it’s ready for anything Mother Nature throws its way. While it offers a selection of uncovered seating, this Dot establishment also has a gigantic greenhouse space that enables all-season sipping. Drinkers can grab drafts and flights of its menu of ever-changing brews and collaborations, as well as cider, alcoholic seltzers and wine for hop-averse folks who are just there for the scenery.

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.

East Cambridge is calling and it’s telling you to get to The Lexington. Overlooking Cambridge Crossing, this modern space resembles an airy greenhouse and open ups to a rooftop patio for seasonal use—a true rarity in this area. The kitchen carefully cranks out hearty, New American fare, making it a prime destination for dinner and drinks. The Lexington is located above its sister eateries Cafe Beatrice and the forthcoming Geppetto, so basically whenever you grab a drink here, you’ll always have dibs on the top bunk.

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 gather around this literal watering hole to cool off during the summer months. Private cabanas cater to the truly indulgent, while most patrons head to the bar to order a frozen cocktail alongside a lobster roll. Closed to the public on weekends, the rooftop is open to non-hotel guests (for a fee) on weekdays.

Trillium’s brews are cherished by locals, especially when you add the outdoor ambiance of the brewery’s spacious Fort Point location. This tap room offers a rotating selection of drafts made on-site, as well as a full-service, farm-to-table restaurant spotlighting local, sustainable ingredients. The rooftop of this Seaport complex is first come, first served, so if you want to get your beer and stracciatella toast fix, you best be ready and eager.

Give your regards to West Broadway when you hit up this South Boston spot. Situated atop the Cambria Hotel, this roof deck provides spanning city views alongside a menu of curated cocktails—shaken and stirred. For bites, this place offers a selection of Italian-inspired dishes with a serious twist (bolognese nachos, anyone?), and its brunch is anything but basic… unless you order the Basic B. Breakfast. Reserve a greenhouse or outdoor table for the ultimate Southie outing.

Felipe’s in Harvard Square has developed a loyal following amongst locals—and for good reason: its fresh, fast and flavor-packed Mexican fare. In the summer heat, the restaurant’s Brattle Street roof deck attracts even more fans, providing prickly pear margaritas, Baja-style fish tacos and a welcomed cool breeze.

Yotel Boston offers a year-round rooftop with panoramic views of the Seaport District and surrounding waterfront. During the winter, guests can seek shelter from our city’s bitter cold inside the bar’s cozy, glass-enclosed seating. The rest of the year, patrons can spread out and make the best of the warmer weather in its sun-soaked outdoor terrace. It’s open daily for your dining, drinking and (on the weekend) brunching pleasure.