Atop the Newbury Hotel lies one of the city’s newer dining attractions: Contessa. Serving up Northern Italian cuisine with views of the Back Bay and Boston’s Public Garden, this glitzy rooftop restaurant has a glass roof with retractable panels for sunny days. Reservations can be hard to come by, so book yours in advance. (In my experience, reservations should be made about a week out.)
1 Newbury St., Boston. 888-974-3948, thenewburyboston.com
Also new to the area restaurant scene is Blue Owl, one of Cambridge’s only rooftop terraces and bars. Located atop the 907 Main hotel in Central Square, Blue Owl has a lounge vibe and an impressive cocktail menu. Ever tried baijiu or aquavit? This is the place to do it.
907 Main St., Cambridge. 617-349-2967, blueowlcentralsq.com
Lookout Rooftop and Bar
Trendy, busy, and central, the Lookout Rooftop and Bar located in the Envoy Hotel in the Seaport is a magnet for downtown workers and thirsty millennials. With views of Boston Harbor and city skyline, it’s hard not to pull out your phone and snap a pic at this spot. I don’t care how many times you’ve been.
70 Sleeper St., Boston (Seaport). 617-530-1538, theenvoyhotel.com
Also relatively new, the Lexington is a Cambridge Crossing spot that opened in October 2020. The bar-restaurant has a roof deck connected to its dining room and is a go-to destination for after-work drinks and evening get-togethers. Boasting an approachable menu of quick bites and entrees, the Lexington is another stylish, breezy rooftop recommendation.
100 N First St., Cambridge. 617-945-1349, thelexingtoncx.com
If you’ve ever been to the Harvard Square Felipe’s, you know it has it all: casual Mexican fare, great margaritas, and tons of space for the reliable crowd this restaurant draws — including a lively roof-deck bar. Enjoy the view as you wash down those burritos and Baja-style tacos.
21 Brattle St., Cambridge. 617-354-9944, felipesboston.com
There are plenty of Legal Sea Foods locations, but the view from the three-story space located on Boston’s Liberty Wharf is unparalleled. Those that visit the third-floor promenade deck will enjoy a four-season rooftop lounge with a retractable glass roof and walls.
270 Northern Ave., Boston (Seaport). 617-477-2900, legalseafoods.com
Earls Kitchen & Bar
Serving up a globally inspired menu with craft cocktails, the rooftop lounge at Earls Prudential Center offers a three-season outdoor patio for guests to take in views of this lively part of the city. The 3,200-square-foot convertible indoor/outdoor rooftop patio features lush plantings, patio heaters, and chic decor.
Earls at the Prudential Center, 800 Boylston St., Boston (Back Bay). 857-957-0949, earlsrestaurants.com
A rarity in Boston’s North End, Ristorante Fiore boasts seasonal rooftop seating, where they serve up classic, homestyle Italian cuisine. Dine on everything from fresh, handmade breads and pastas to classic, old-world Italian plates and seafood dishes.
250 Hanover St., Boston. 617-371-1176, ristorantefiore.com
Located on the rooftop of the Cambria Hotel in South Boston, Six West is often bumping. The crowd tends to linger longer here because the views are stunning. It draws a diverse crowd of professionals, and leans slightly on the swankier side. There’s a full bar and plenty of inventive cocktails.
6 West Broadway, Boston. 617-752-6681, sixwestbroad.com