Two glasses of beer in focus with blurry people in the background.

A Guide to the Top Outdoor Bars in Boston

Published on June 7, 2024


As the sun casts its golden glow over the Charles River and the city gears up for another summer, Boston's outdoor bars become the epitome of sophisticated leisure. Imagine sipping a perfectly crafted cocktail while gazing at panoramic views of the skyline, or savoring a glass of wine as the sea breeze from Boston Harbor cools you down. In this guide, we'll explore the crème de la crème of Boston's outdoor bars, where impeccable service meets breathtaking ambiance. Whether you're looking to unwind after a day of exploring the city's rich history or simply enjoy the vibrant atmosphere, these venues offer an elevated experience that marries luxury with the warmth of an open-air setting. Join us as we uncover the best spots to indulge in the finer things while embracing the beauty of Boston's summer nights:

  • Wedding Party toasting glasses of beer at the beer garden

Trillium Garden On The Greenway

Beginning with a stop at Trilium Garden, on the Rose Kennedy Greenway. The beer selections at Trillium Garden are a connoisseur's delight, featuring a rotating array of Trillium's finest offerings. From crisp, refreshing lagers to complex, aromatic IPAs, each pour is a testament to the brewery's dedication to innovation and excellence. Whether you’re a seasoned beer aficionado or a casual enthusiast, the knowledgeable staff is always on hand to guide you through their latest creations, ensuring a personalized and memorable experience. From Tuesday through Sunday, indulge in a culinary journey with a variety of food trucks serving delectable bites from diverse cuisines. Expect to meet plenty of friendly dogs, as Trillium Garden warmly welcomes all leashed dogs to the Greenway.

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  • Outdoor event with a crowd, food truck, and modern buildings.

Cisco Brewers

If you find yourself in Seaport, you’ve got plenty of bars to try, and yet Cisco Brewers manages to shine through. At the heart of Cisco Brewers is an impressive selection of craft beverages that cater to a wide range of tastes. From their renowned beers and refreshing hard ciders to their exquisite wines and handcrafted cocktails, every sip is a testament to their commitment to quality. In the summer you can expect to find their “Summer Rays Golden Ale”. Year round, their delightful “Wandering Haze Hazy IPA”, “Grey Lady Wheat Ale”, “Whale’s Tale Pale Ale”, and their “Shark Tracker Light Lager”. Additionally, be sure to treat yourself to their newest IPA, “Peached Whale”. The bartenders are not just servers but connoisseurs, eager to guide you through their diverse offerings and help you discover new favorites.

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  • An evening at a rooftop bar with people socializing, overlooking a cityscape and waterfront.

Lookout Rooftop

Equally worth mentioning is the Lookout Rooftop at the Envoy Hotel. Whether you’re celebrating a milestone, enjoying a romantic evening, or simply unwinding after a long day, the Lookout Rooftop at the Envoy Hotel offers an unparalleled experience. It’s a place where the elegance of luxury meets the ease of accessibility, creating a unique haven high above the hustle and bustle of the city. While you’re there be sure to indulge in their Signature Series Cocktails, such as the “White Lotus”, “Caribeno”, or the “Yuzu Cute”. If you’re in the mood for an IPA, we recommend you try the “Harpoon IPA”, or the “Blue Comet!” Remember to browse their bites menu and order a savory flatbread, or uniquely delicious tacos. At the Lookout Rooftop, every moment is a memory in the making, set against the stunning backdrop of Boston’s ever-changing skyline.

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  • People standing on a dock near a boat, enjoying a sunny day.

The Tall Ship

As if we couldn’t get closer to the ocean, we can hop aboard The Tall Ship. Stationed along the harbor, this majestic three-masted, once sailed schooner transforms dining into a luxurious journey. The vast views of the Boston skyline and serene waters create a picturesque backdrop, perfect for romantic evenings, celebratory dinners, or stylish gatherings with friends. The Tall Ship in East Boston offers an unparalleled waterfront luxury experience with its exclusive private lounge area. With an extensive list of beverage offerings, savor a craft cocktail such as their “Knotty Nauti”, “Painkiller” or an “All Aboard”. Each reservation spans 3.5 hours, providing ample time to bask in the stunning harbor views and enjoy the sophisticated ambiance. The lounges are designed to host intimate gatherings, comfortably accommodating between 8 to 15 guests.

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