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The best Boston rooftop bars you need to know about

Hip hotels, neighborhood hangouts and waterfront decks; these Boston rooftop bars deliver views with a side of booze

By Eric Grossman and Time Out Boston Staff |
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The Colonnade
Photograph: Courtesy The Colonnade The Colonnade’s rooftop pool and bar

Boston's buzziest rooftop bars cut across demographics and interests; depending on when you visit, you might encounter hordes of office workers or selfie-snapping coeds. One thing's for sure: Whenever New England’s notoriously fickle weather allows, local residents head in droves to alfresco drinking spots. And Boston’s best rooftop bars let you take your fun to a higher level. We’ve rounded up the the most stellar ones in the area, from the Back Bay and North End to Harvard Square. Escaping to a rooftop bar is a great way to decompress after a long day at work or watching a stressful game at one of the best sports bars in Boston. So when you need to come out of your Boston dive bar hibernation, or merely want to catch some rays, this is where to go.

RECOMMENDED: Full guide to the best bars in Boston

Best rooftop bars in Boston

1
Lookout Rooftop
Photograph: Courtesy Lookout Rooftop
Bars, Hotel bars

Lookout Rooftop and Bar

Seaport District

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 Rockland Trust Bank Pavilion.

2
YOTEL
Photograph: Courtesy YOTEL
Hotels

Sky Lounge at YOTEL Boston

Seaport District

YOTEL Boston offers a year-round rooftop terrace with panoramic views of the city from its perch in the Seaport District. During the winter, guests feel like they're at a ski resort thanks to heaters, plush blankets, and purple hot water bottles. When the weather is warm, area workers and residents fill the terrace to catch some rays. Friendly staffers and fine food and drink complete the experience.

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3
Rooftop@Revere
Photograph: Courtesy Rooftop@Revere
Bars, Hotel bars

Rooftop@Revere

Bay Village

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.

4
Legal Harborside 3rd Floor
Photograph: Courtesy Legal Harborside/Chip Nestor
Restaurants, Seafood

Legal Harborside

Seaport District

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.

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5
The Colonnade
Photograph: Courtesy The Colonnade
Hotels, Boutique hotels

Colonnade Hotel

Back Bay

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.

6
Coppersmith
Courtesy Yelp/Cristina R.
Restaurants, Contemporary American

Coppersmith

South Boston

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.

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7
Pier 6
Courtesy Yelp/Pier 6
Restaurants, Seafood

Pier 6

Charlestown

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.

8
Daedalus
Photograph: Courtesy Creative Commons/Flickr/Sarah Ross
Restaurants, Contemporary American

Daedalus

Harvard Sq

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.

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9
Felipe's Taqueria rooftop
Photograph: Courtesy Yelp/Neechi M.
Restaurants, Mexican

Felipe’s Taqueria

Harvard Sq

Felipe’s in Harvard Square is almost always packed, and for good reason: fresh, authentic, and fast Mexican fare. In the summer, the roof deck attracts even more fans, where you can enjoy fresh-squeezed key lime margaritas, nachos, and a cool breeze.

10
Ristorante Fiore
Photograph: Courtesy Ristorante Fiore
Restaurants, Italian

Ristorante Fiore

North End

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.

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11
Baseball Tavern
Photograph: Courtesy Baseball Tavern
Bars, Sports Bars

Baseball Tavern

Fenway/Kenmore

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. 

12
Sinclair rooftop
Photograph: Courtesy Yelp/Sam H.
Music, Music venues

The Sinclair

Harvard Sq

This Harvard Square music hall, booking nationally-renowned musicians nightly, is a classier option among music venues in the area. It even has a restaurant serving elevated American comfort fare. The restaurant's rooftop terrace is perfect for a pre-show cocktail.

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13
Earls Kitchen + Bar
Photograph: Courtesy Yelp/Earls Kitchen + Bar
Restaurants, Canadian

Earls Kitchen + Bar - Prudential Center

Back Bay

Earls is a Canadian chain offering an extensive, globally-inspired menu of comfort food. The Prudential Center location has a three-season rooftop bar that's often packed with Back Bay office workers and flocks of conventioneers.

See the best rooftop bars in America

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