Only a decade ago, finding open-air bar service with a bird’s-eye view in Boston was akin to stumbling upon a Yeti in the rainforest. But these days, things are looking up. Sky-high oases take all forms in nearly all neighborhoods, from casual, caps-are-okay Baseball Tavern in Fenway to Fort Point’s super-chic, must-wait-in-line-to-get-in spot Lookout Rooftop & Bar. What is it that makes craft cocktails, fruity umbrella drinks and local drafts taste better while one’s warming in the sun (or chilling under the stars) and enjoying city skylines and oceans views? The atmosphere. Definitely.
South Boston’s only roof deck (aka Airdeck), this 3,000-square-foot al fresco space is outfitted with a vintage Airstream trailer-turned-bar, rustic chic picnic tables, and stellar cityscapes. Working millennials, post-college grads and city dwellers dig into #PitcherPerfect cocktails like Peach Tree and Cheerwine slushies spiked with Bulleit Bourbon. Chef Jason Heard’s whims range from foot-long hot dogs and canned local brews to barbecue from the nine-foot Lang Smoker.
Poe’s Kitchen at the Rattlesnake
With its “south of the border”-inspired menu designed by beloved Chef Brian Poe, the rooftop at Poe’s Kitchen at the Rattlesnake skews toward young professionals who love a little spice in life. High above the Back Bay scene, this is the perfect place for a carafe of sangria in the sun, a margarita or two, some creative tacos and full-on Latin-style fare.
The Lookout Rooftop & Bar
Poised above Boston as part of the new super trendy Envoy Hotel, this is the quintessential bird’s eye view of city and sea. There’s an exclusive yet relaxed vibe with cozy couches, high-design heat lamps for chilly evenings, glowing fire pits, and a cool railing bar. Look out for refreshing concoctions like Juliet and Romeo (gin, mint, cucumber and rose water) or Not Too…Modest (citrus vodka, Cointreau raspberry and bubbles).
Rooftop @ Revere
Situated high above Boston’s Theater District, the posh hotel’s chic open-air lounge is true adult fun in the sun, complete with its own waving monkey art installation. Must-sip summertime libations include the refreshing Boston Common Cucumba and the island-inspired Stuart Street Sip n' Slide, and a special Harpoon brew was recently created exclusively for the Rooftop @ Revere. Lounge on comfy day beds (first come first served) for super chic seen-and-be-seen status.
The Baseball Tavern
Sports fans revel in the roar of the crowd at this roof deck that actual overlooks the home of the Boston Red Sox. Located literally a fly ball’s throw from historic Fenway Park, you’re in your own baseball park setting—bench style seats, banners and score board décor. Enjoy a frosty beer, classic deep-fried bar food, a fried whole belly clam plate and the background sounds of the Boys of Summer.
This Charlestown hotspot’s recent renovation translates to not one but two outdoor areas—an intimate 30-person roof deck and a larger downstairs deck with a lounge, both with breathtaking waterfront views. The “Nantucket in the city” crowd pulls up on boats and water taxis, as they stroll in for the fresh-off-the-boat seafood and refreshing cocktails like the Captain’s Mistress, the Pier 6 Mai Tai or the Castro Smash.
A giant global wine list awaits you on the North End’s only roof deck. Looking down on bustling Hanover Street, this get-away is complete with a mural of Italy, strings of twinkle lights, a brick-back bar and a retractable roof. Pair your classic Italian cuisine (think fresh, handmade breads and pastas alongside old-world dishes) with a glass of sparkling rosé, prosecco or a full-bodied chianti.
With bragging rights to one of the city’s largest roof deck, Legal’s three-story flagship location is topped off with picturesque city skyline and harbors views. The roof’s glass walls and ceilings retract during warmer temps, so you can hang out under the stars while sipping cocktails and ordering fresh seafood. The cocktail list keeps its young professional clientele happy with innovative drinks such as adult “slushies.”