City Spotlight: Best Rooftop Bars in Boston

With a mix of classic, ornate buildings and modern skyscrapers appearing on either side of the iconic Charles River, the Greater Boston skyline is one of a kind — and what better way is there to enjoy it than while sipping on a cocktail at a rooftop bar? There’s plenty of spots where you can take in the city’s sweeping views, and we’ve rounded up our favorites — whether you’re looking for an unforgettable night out or a laidback summer hang.

Read on for our list of the six best rooftop bars in Boston.

The Stratus Cocktail Bar. Photo by Atlantic Pictures.

800 Boylston Street, Boston

The newly opened View Boston replaced the Top of the Hub on the top three floors of Boston’s Prudential Center — and brought with it breathtaking views of the entire city through floor-to-ceiling windows and a panoramic, open-air viewing deck, as well as a cocktail bar, restaurant, and event space. At The Stratus, you can enjoy a handcrafted cocktail among the clouds, while watching the sunset over our fair city. You’ll need to buy tickets to View Boston to get here (ranging from $34.99 for no-frills, general admission to $64.99, which includes $12 towards food and drink and a guided tour).

However, right now, you can win two free tickets to View Boston on our Instagram page. That’s right — head over to @AptAdvisorBOS on Instagram, check out the guidelines on our pinned post, and enter to win two free tickets to see the best View of Boston from one of its highest points. Free to enter, free to win.

70 Sleeper St., Boston

With a location that’s pretty much as close to the water as you can get, Lookout Rooftop has one of the best skyline views in Boston. With fire pits and cozy couches, this beverage-only roof deck bar is perfect for an intimate date night or a fun night out with friends. The bar features covered and uncovered seating areas, as well as heaters for cool evenings — and even heated igloos for the winter — making it a year-round destination to see views of the Fort Point Channel and Boston Harbor.

120 Huntington Ave., Boston

Did you know there was a rooftop pool in Boston? This iconic spot on top of the Colonnade Hotel is open to the public from 9 AM to 9 PM on Monday through Thursday, and from 2 PM to 9 PM on Sundays. The entrance fee is $50 for members of the public and accessible on a first come, first served basis. There are also private cabanas available to rent. Take a dip on a hot summer day, enjoy small bites, and have delicious cocktails at a place unlike any other in the city.

Over the Charles Rooftop Bar. Photo courtesy of DoubleTree Suites by Hilton Boston–Cambridge.

400 Soldiers Field Rd., Boston

The rooftop lounge at the DoubleTree Suites in Lower Allston, right over the bridge from Cambridge, delivers on the promise of its name. Sit on one of the comfy couches at Over the Charles and feel like you’re floating over the river, while watching the sunset over Cambridge and enjoying a classic New England lobster roll. Come on Wednesday for Trivia or on Thursday for live music. And if you’re a jazz fan, the Scullers Jazz Club is right inside.

21 Brattle St., Cambridge

Rooftop bars usually bring with them an air of opulence — but if you’re looking for a spot where the food and drinks are as unpretentious as they are delicious, then you’ll want to snag a table at Felipe’s rooftop seating area in Harvard Square. Don’t be fooled by the fast-casual taqueria’s first floor; after grabbing tacos downstairs, head up to the rooftop patio where you can drink in the views of Cambridge and Boston with a margarita in hand. Authentic Mexican food and a great view — what else do you need?

Dorchester Brewing Company Tap Room rooftop patio. Photo courtesy of Dorchester Brewing Co.

1250 Massachusetts Ave., Boston

Featuring a four-season, enclosed “Hopservatory” on its rooftop in addition to an outdoor patio, as well as a wide variety of craft beers on tap, hard cider, slushies, seltzers, wine, cider, and non-alcoholic beverages, Dorchester Brewing isn’t your typical brewery. The Tap Room also has classic games like pinball and Skee-Ball, free Wi-Fi, and fresh barbecue served up by M&M BBQ, on-site daily.

200 Stuart St., Boston

No list of Boston rooftops is complete without its largest rooftop lounge — the rooftop located at the Revere Hotel right in the center of Boston’s vibrant downtown. Everyone can find something they like at the Rooftop@Revere, as the menu spans from elevated dishes like the Brûléed Brie to classic American dishes like the Rooftop Cheeseburger. Take your chance to stand on top of the City on The Hill, across the 15,000 square feet of this classic rooftop.

Legal Harborside exterior and rooftop bar. Photo courtesy of Legal Sea Foods.

270 Northern Ave., Boston

The third-floor rooftop of the flagship location of Legal Sea Foods is the perfect spot for fresh seafood, waterfront views, and fun and casual dining. The retractable glass roof and walls allow for all-weather fun in an iconic location, and the Legal Harborside rooftop is an unbeatable spot to catch the sunset.

6 West Broadway, Boston

One of Southie’s newest rooftop bar, Six West is one of the best places to see the Boston skyline, whether it’s over a delicious brunch or lite Italian-inspired bites and cocktails. This swanky spot. located right at the entrance to South Boston, is open year round, with heated igloos that crop up during the winter.

To see more of our favorite spots in Boston, follow us on Instagram at @AptAdvisorBOS, where you can see tips on renting in Boston, learn about hidden neighborhood gems, find out about new listings first, and win free giveaways. Enter our latest giveaway to win two free tickets to View Boston here.

Header photo of The Stratus by Atlantic Pictures.