The 21 best rooftop restaurants and bars in Boston

Raffles Boston knows that nothing pairs better than the luxury hotel's signature Singapore Sling and city views—and at its Long Bar and Terrace, you get both. Located within the five-star Back Bay establishment, this restaurant and bar is open from sun up to way past sundown, serving everything from an early morning business breakfast to cocktails capping off a night on the town. Whether you choose to sit inside, where floor-to-ceiling windows allow you overlook the South End, or outside on the terrace, this mid-century modern masterpiece will be easy on the eyes.

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; the roof is retractable (making this spot a hit in all seasons); 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.

Perched atop the popular Envoy Hotel, this trendy eighth-floor eatery and bar offers small bites and upscale cocktails from the comfort of stylish lounge seating—but its real draw is a dazzling skyline view that makes wait times worth it. Come for the sunset panorama over Fort Point Channel, and stay for the Seaport Sangria and tunes as you mingle with downtown's in-crowd. Pro tip: Go big and reserve the firepit table.

This 51st-floor indoor-outdoor rooftop restaurant and cocktail lounge in the Prudential Center is the highest outdoor bar in all of Boston. Part of the Pru’s three-floor observatory, the airy space is connected to The Cloud Terrace (a 360-degree open deck) and serves small plates, wine and cocktails alongside its panoramic birds-eye view of the city. Word to the wise: Just don’t look down if you’re afraid of heights.

Hovering above the Theater District and Back Bay, this hotel hotspot offers one of the liveliest rooftop scenes in the city come summer. It’s also one of the largest at 15,000 square feet, but that doesn’t mean it doesn’t get full—it’s one of the most sought-after refuges in town, so be sure to reserve a spot beforehand. Whether you’re there to crash by the bar or hang out in the lounge, you’ll be able to enjoy the spectacular views in all of their 270-degree glory. Don’t forget to order the special ice cream sandwich of the day.

Open year-round, the Lifted Restaurant at The Omni Boston Hotel at the Seaport brings easy breezy city vibes with its rooftop digs and tropical 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 crispy Brussels sprouts—to more substantial plates made for sharing (or solo eating, if you’ve worked up an appetite doing laps), such as the salted caramel lobster roll. Wash down everything—high-rise vistas included— with an icy beverage from its extensive selection of frozen drinks.

Located atop The Newbury Boston, this elegant eatery serves more than just comforting Northern Italian fare—it also serves looks in a major way. Befitting of a special occasion or celebratory dinner, 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 art deco-like interior, 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.

East Boston’s seasonal roof deck is a neighborhood gem with a relaxed, unpretentious atmosphere—but it’s cozy, so make reservations in advance to ensure your harborside views. Reminiscent of a shipping container and with plenty of nods to the East Boston Shipyard, this nautical spot serves American classics with an emphasis on seafood, including shrimp and grits, seared scallops and lobster benedict for brunch. Grab a craft beer from the walk-up window bar and say cheers over Eastie.

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 like steak frites and fish and chips, and a list of classic cocktails, it’s the perfect place to temporarily escape the city’s chaos.

If you’re chasing water views, you’ll certainly find them at Pier 6. Located near Charlestown’s Navy Yard, this marina rooftop provides arguably the most incredible panorama of the Boston skyline. A lively mix of locals typically congregate on the nautically themed deck to get their fill of fresh seafood and New England classics. A well-stocked bar is on hand to keep everyone hydrated as they drink in that salt air.

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.

Rooftops don’t have to be ritzy to be amazing. Case in point: Cityside Tavern’s laidback deck perched above Cleveland Circle. A hotspot amongst college students and Green Line residents, this place serves up elevated pub grub and drinks with an airy ambiance. Here, you can down dive bar classics (think wings and trays of nachos), as well as more sophisticated spins of tavern favorites, like the short rib grilled cheese and Hot Bird southern fried chicken sandwich. On the weekends, brunch here is a must, nurturing locals with items like batches of french toast sticks, hash-covered hangover skillets and indulgent innovations like breakfast egg rolls and Cinnabon pancakes.

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 made on-site, as well as cider, alcoholic seltzers and slushies (and wine for hop-averse folks who are just there for the scenery). Pair it all with barbecue from on-site restaurant M&M, including “dumpster fries” piled high with barbecue pulled pork and cheese sauce.

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.