Top Boston Rooftop Bars: Where to Sip + Soak in the City Skyline

Whether you’re dining or just raising a glass, those who want to savor this awesome weather before the clocks turn in Boston have a plethora of options. Think Italian, sushi or BBQ, with craft cocktails and local brews to boot. Here are the top Boston rooftop bars — and a preview of what you’ll see.

Lookout Rooftop + Bar at the Envoy Hotel
Lookout may be perched high above Boston’s hottest neighborhood for nightlife, but if you don’t line up by about 4PM in the afternoon the line may snake around the block for the stunning Seaport views at this trendy newcomer. Head bartender Michael Ray works together with Beantown brewery Harpoon and local spirit makers like GrandTen for WireWorks gin and Bully Boy for rum, vodka, and whiskey to craft artisanal cocktails. The latest seasonal hit — the Rum for Your Life, with pineapple, lime, and simple syrup — celebrates the last blast of Indian summer. Views through modern glass walls offer a prime panorama of the city skyline and Boston Harbor. Post-game with noshes like tuna poke, flatbreads, and locally caught scallops from chef du cuisine Tatiana Rosana at Outlook Kitchen and Bar, also at Envoy Hotel. Make a reservation at Outlook Kitchen and Bar.

Boston Rooftop Bars

Legal Harborside
Good things come in threes at Legal Harborside, where the trio of sangrias (red, white, and strawberry) are the perfect way to toast the all-seasons rooftop bar and lounge —and three very different dining experiences on each floor. The first is a casual concept with “picnic tables” and a market, the second offers fine dining and an interior reminiscent of a ship’s dining room, and the third is the cherry on top: a four-season space with a copper fireplace and retractable glass walls and ceiling just right to admire those harvest moons glimmering over the marina. The adult slushies and Top Deck Margarita are the top choices to wash down a menu focusing on sushi and oysters. Make a reservation at Legal Harborside.

Boston Rooftop Bars

Coppersmith
Though the vintage airstream trailer converted into a bar may be the most memorable décor on the Coppersmith roof deck, the drinks are far removed from the Solo cup beverages found in most double-wides. The mood is festive and casual, especially this fall as football lovers get a kick on Sunday and Monday game days when executive chef Jason Heard busts out a “rivals menu” including regional fare from the New England Patriots’ opposing teams including pierogies from Cleveland and crab cakes from Baltimore. Hungry for more? The Air Deck is the only space you can order “Air Deck Picnics,” family-style bites like BBQ, tacos, and sliders served up in vintage Radio Flyer wagons for 6-20 people (must be ordered in advance). Make it a party and tap your toes to live music being offered Sunday afternoons on the deck from 4-7PM, too. Make a reservation at Coppersmith.

Boston Rooftop Bars

 Top of the Hub
Top of the Hub may be in the heart of the Boston, but the drink menu hits are straight up Caribbean. Lead bartender Arley Howard serves up frothy pina coladas in a city largely devoid of frozen cocktails, in addition to a plethora of mojitos. One of the most popular tipples is the Level 52 — so named for the floor the restaurant occupies in the landmark skyscraper of the Prudential Center — featuring vodka and Chambord topped with Champagne in an ice-cold martini glass with raspberries. It’s great to raise a toast to the stunning views across Boston Harbor up to 80 out, and try one of the more than 3,000 bottles of bubbly or wine in the Hub’s two large wine rooms. Any and all drinks are a terrific way to get those dancing feet loosened up for live music or as a precursor to new executive chef Stefan Jarausch’s menu, which changes seasonally. Make a reservation at Top of the Hub.

Boston Rooftop Bars

Ristorante Fiore
Ristorante Fiore prides itself on classic Italian fare, and though the food is what your nonna may have served up, the view is anything but. Tucked away in a hidden alcove of the North End — Boston’s bustling Little Italy — the intimate roof deck has a bar and a smattering of tables for just the right amount of background buzz and sexy conversation. Try the handmade breads and pastas, savory gnocchi with sausage, or seasonal seafood dishes locally sourced from the nearby Atlantic. Though the deck is only open after 4PM, those strolling this charming neighborhood mid-day can take advantage of the speedy, year-round business lunch menu, picking one to three courses for $15, $20, or $25. Make a reservation at Ristorante Fiore.

Boston Rooftop Bars

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Carley Thornell is a travel writer whose experiences eating street food in Japan, English peas in the UK, free-range steak in Argentina, and Brussels sprouts at Estragon tapas in her hometown of Boston have provided unforgettable culinary inspiration. Shout out at carleythornell@gmail.com.

Photo credits: Chip Nestor (Legal Harborside).