A Beloved Boston Bartender Shares His Favorite Local Drinking Spots

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You know how to EAT THIS CITY. With top chefs as tour guides, you’ve learned how to scout out hot spots for breakfast and brunch, where to go for a delicious date night, and how to feast like a local liege in the cities you love. But where do you wash it all down? Do you know how to find the best brewpub? Uncover who makes the meanest bloody marys and the most sparkling mimosas?

You’re about to find out. Welcome to DRINK THIS CITY!

This week we’re in Boston, indulging our passion for rooftop bars, at The Envoy’s incomparable Lookout Rooftop. Recently renovated, Lookout is summertime drinking goals personified. The cocktails are handcrafted and visually stunning, the panoramic views of the Boston skyline are breathtaking (they’ll look killer in your Instagram feed), and the newly added Harbor Lounge offers plush seating and a little privacy. If you’re in Boston during the summer months, this is where you want to be.

It turns out, Lookout is also where you want to be in the winter. While other rooftops get chillier and shut down for the season, things just get hotter at Lookout. On offer are specialty coffee drinks and mulled wines, and guests are invited to drink them while they warm up inside beautifully lit, 10-seat Igloos. The giant glowing snow globes turn Lookout Rooftop into a dazzling winter wonderland.

As head mixologist at Lookout Rooftop, Brian McDougall is perfectly positioned to take us on an incredible tour of Boston’s best bars. But first, let’s take a look at his creations!

Via Lookout Rooftop at The Envoy

You feeling thirsty? Let’s go and drink this city!


Ward 8

Bacon-infused Bloody Mary at Ward 8. Ward 8 has a small neighborhood feel with the posh finishes of a high-end restaurant.


Lolita Seaport. Everything Mezcal! Lolita has a robust selection of all things tequila, their mezcal selection is second to none.