The season for enjoying drinks outdoors is a short-lived one in Boston, so everyone makes the most of it. Bars and restaurants provide heat lamps and blankets — even in summer the weather can be fickle. The city’s only rooftop pool bar at The Colonnade Hotel allows you to rent your own cabana for the evening. Spots with prime real estate on Newbury and Boylston streets, and those with waterfront settings, are usually packed with patrons enjoying al fresco drinks and snacks. Here’s where you can make the splashiest toast under the stars.
The Colonnade Rooftop Pool
There’s only one rooftop pool bar open to the public in Boston and it’s at The Colonnade Hotel on Huntington Avenue. Happily, this year it has loosened up the public access a bit, which means it’s now a fun and lively venue for more people to be to watch the sun go down. For more privacy and space, rent a cabana, which can accommodate up to six guests. Changing rooms and showers are available for when you are ready to take a dip in the water. A variety of cocktails, plus dishes like lobster rolls and pizza — this is the only hotel in the city where the North End’s famous Regina Pizzeria is on the menu — make for a memorable night.
This Forbes Travel Guide Four-Star hotel, which sits on Boston’s waterfront, is a picture-perfect spot that overlooks Fort Point Channel. During the summer, the Five-10 Waterfront patio bar is always hopping. Enjoy clever rum concoctions from RumBa, the city’s premier rum and champagne bar. RumBa’s menu, led by head mixologist Dragan Gajica, features signature cocktails like the Boston Tea Party (cinnamon and orange spice tea-infused Bacardi, lemon juice, honey, egg whites and tea leaves), which was created by Gajica himself. You can also expect perfectly made mojitos and caipirinhas. Don’t be surprised to see passersby turn around and make a beeline for the outdoor bar. It’s too enticing to pass up.
Bar Boulud Boston
Located in the Five-Star Mandarin Oriental, Boston hotel on Boylston, Bar Boulud Boston may not have the largest patio — it’s wide enough for tables of two — but sometimes cozy is all you need. Consider this your French-inspired bistro to toast a friend or share a romantic dinner. You’ll be front and center for entertaining people-watching while enjoying fine wines from sommelier Joe Camper’s curated list and sampling dishes from world-renowned master chef Daniel Boulud’s menu. The charcuterie, house-made pâté and terrines are all lovely warm-weather options.
Stephanie’s on Newbury
A mainstay on the road natives lovingly refer to as “The Street” since it opened 21 years ago, Stephanie’s patio is the place to see and be seen. Newbury Street is always an endless parade of locals and visitors, there to sightsee, shop, dine, drink and simply soak up the vibe of Boston’s high-end shopping district. Once you order a warm-weather drink like the Texas Mule (watermelon-infused vodka, ginger beer, fresh lime, garnished with a fresh watermelon slice) or Stephanie’s Coronarita (tequila, triple sec and house-made sour served with an inverted Corona pony) with a dish like lobster guacamole or chilled gazpacho, you’ll hope summer never ends.
Another picturesque property, Battery Wharf Hotel, Boston Waterfront, is situated right along The Hub’s scenic HarborWalk and offers a delightful outdoor terrace. Come nightfall, you can book a table that comes with your own personal fire pit, sip on drinks, order a delicious Vermont cheddar cheese fondue or make-your-own s’mores. Comfortable couches and Adirondack chairs (wool blankets are available on those windy nights) invite relaxing and watching the world go by.