As Bostonians, we endure painfully long (and cold winters!), so I anxiously anticipate the warm weather and even more so, the al fresco dining and imbibing! Now that summer is in full swing, you can bet that I am out and about enjoying the gorgeous summer days with a cocktail in hand.
Boston is beautiful in the summer and what better way to enjoy a warm evening than on a rooftop?! While I spend a great deal of time enjoying my own apartment’s roofdeck, I absolutely love visiting my favorite Boston rooftop bars and restaurants on a summer night.
If you’re looking for a rooftop spot to enjoy on the next gorgeous day, I’ve rounded up my favorite spots to savor a cool libation or delicious meal under the summer sun. Cheers!
The A-Lyst for Boston’s Best Rooftop Bars and Restaurants
Lookout Rooftop Bar at The Envoy Hotel
It took me almost a year after The Envoy Hotel opened to finally make it up to the Lookout Rooftop Bar because every time I tried to go, the line was too long! Located in Boston’s bustling Seaport District, the Lookout rooftop is just that…bustling…with young professionals, the after work crowd, and tourists, but let me tell you, the view cannot be beat! With downtown Boston and Boston Harbor as your stunning backdrop, you can enjoy delicious martinis, while watching the hustle of Seaport Boulevard below you. My recommendation is to come early on a weeknight (think 5pm and a Monday-Wednesday is ideal) and make sure to stay until the sun sets, as the view is absolutely gorgeous! 70 Sleeper Street, Boston, MA 02210
If an al fresco Italian meal under a canopy of white string lights is your idea of a perfect date night then head over to Hanover Street and grab a seat on the rooftop patio of Fiore. Fiore’s roof offers diners the perfect blend of classic North End Italian and quaint outdoor city dining. My go-to is always the Bombolotti al Forno (homemade pasta with spicy Italian sausage, onion, tomato sauce, basil, reggiano and goat cheese) and one of the restaurant’s signature cocktails – they are yummy and strong! 250 Hanover Street, Boston, MA 02113
If I’m heading over the river to Cambridge, I love hitting up Daedalus for a casual rooftop dinner. For fans of al fresco dining, this Harvard Square staple is a great choice for burgers, wings, hearty salads, and drinks. Essentially, you can enjoy all of your favorite ‘pub-style’ food in a relaxed outdoor setting…a total win-win! 45 Mount Auburn Street, Cambridge, MA 02138
With unobstructed views of the ocean, a fireplace to warm you on chilly New England nights, and a menu boasting sushi and delicious cocktails, there are many reasons to love the rooftop of Legal Harborside. This 20,000 square feet flagship property for the restaurant group offers three floors of dining with a killer rooftop restaurant at the top. The roof is always hopping and always a blast! Whenever we have friends visiting from out of town, this is where we take them because it offers a little bit of everything that I love about Boston in one great spot; summertime outdoor dining, seafood, and of course, great drinks! If you have a group, go early to avoid the lines and try to snag one of the lounge areas! 270 Northern Avenue, Boston, MA 02210
With so many of my friends living in South Boston, I frequently find myself in the neighborhood, and can’t help but love the laid back vibe of Coppersmith. Offering two food trucks, plenty of TVs, and a vintage Airstream that serves rooftop libations (yes, really!), this restaurant/bar is truly different than anything else in the city! Located off the beaten path on the west side of Southie, Coppersmith is definitely worth checking out on a summer night. I can promise you many 20 and 30-somethings and plenty of booze! 40 West 3rd Street, South Boston, MA 02127
Other spots worth checking out…
The Colonnade Hotel’s Rooftop Pool & Lounge
Have an extra day off from work? If you go to The Colonnade Hotel’s rooftop pool Monday-Friday, you can purchase a day pass for $45.00. I’ve done this before and let me tell you, it’s glorious sitting up there and reading a book while enjoying endless frozen cocktails with a gorgeous view of the Prudential Center. Oh, and you can swim, too! 120 Huntington Avenue, Boston, MA 02116
Back in the day, Felipe’s was known for its late night fare (I definitely made the trek over there for a 1am burrito more than once!), but now it is one of Harvard Square’s best rooftops! Several years ago, Felipe’s expanded into a new space and added an amazing outdoor space. Come to enjoy inexpensive margaritas and Mexican fare — leave happy and full! 21 Brattle Street, Cambridge, MA 02138
If you’re in the Charlestown neighborhood and in the mood for seafood and a view, the rooftop of Pier 6 should be your destination. The restaurant, which serves up classic New England dishes like chowder, lobster rolls, and fried calamari, provides an unbelievable view of the Boston skyline and waterfront. 1 8th Street, Charlestown, MA 02129
Outfit Details:
Dress: Who What Wear Ruffle Dress (available at select Target stores and under $40!)
Lipstick: Bobbi Brown Art Stick Liquid Lip in Pink Punch
Nail Polish: OPI Small and Cute
Handbag: Fendi Peekaboo in Royal Blue
Sunglasses: J.Crew Factory Classic Sunglasses (old; similar here)
The A-Lyst is a Boston-based lifestyle blog curating the very best of style, beauty, food, and travel.