Boston’s Best Al Fresco Dining

Al fresco dining season is in full swing in between the record rain. While getting reservations for outdoor seating can be challenging, from first hand experience, it’s definitely worth a try. Here are five of the newest spots to dine outside (or open air) in Boston.


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Sitting high on the rooftop of The Newbury (aka the former Taj), Contessa draws its aesthetic from northern Italian estates and old European resorts. From the roof, you can look out onto Newbury Street and the Boston Common, and retractable panels transform the space into an open-air restaurant. The food and drinks are equally as amazing as the scene, as Contessa is brought to us by the same restaurant group as the (almost) impossible to get a reservation, Carbone, in NYC.


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Toro is a staple for authentic Spanish tapas in the South End, but since COVID, they have expanded their space outdoors thanks to a vacant lot and a furniture donation from Wayfair. The outdoor space includes lots of greenery and some lounge seating around fire-pit tables, as well as a mix of other seating options. And, of course, their signature food and drinks have kept people coming in for years.

Woods Hill Pier 4

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As the name suggests, Woods Hill’s outdoor dining space is located on the pier offering stunning harbor views in addition to a delicious, farm-to-table menu. They were even able to maintain the outdoor dining option throughout the seasons as they offered igloos ( for a price!), for social distancing initially but also cooler temps.


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This Venetian-style osteria and wine bar features an al fresco courtyard, which is enclosed by the South End’s ivy-covered brick walls. It serves as the perfect backdrop for date night or catching up with friends.

Tall Ship

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This spring, an actual floating oyster bar/pop up experience opened in East Boston. There are gorgeous mahogany bars, a raw bar, and nautical- themed cocktails. Next door, there’s a 40,000-square-foot outdoor space that will host live entertainment, retail and food vendors, food trucks, and pop-ups. It is definitely worth the trip to East Boston!

Let me know your favorite al fresco dining spot in the comments!