The Best Spots to Enjoy Happy Hour on Nantucket

On Nantucket, the fun doesn’t end when you step off the beach. With so many restaurants using happy hour specials to compete for crowds, there’s plenty of fun to be had before the sun even sets.

Discounted drink specials and local bites start setting the stage for the island’s nightlife as early as 3 p.m. From elegant cocktails and ice cold local brews to open-air patios and intimate wine bars, choosing the atmosphere that matches your mood is easy.

So start exploring the best day-drinking deals in town and enjoy happy hour on Nantucket.

Cisco Brewers

cisco brewers

Keep the flip-flops on. Beach clothes are welcome at Cisco Brewers, where locals and visitors gather from all across the island.

See the best in local music here with live performances all summer long— and with tables under the sun, chilled beer and gourmet finger-food, Cisco embodies the true spirit of an island happy hour. Play cornhole on the grass while you sample local brews and flights, wine, or creative cocktails from Triple Eight Distillery. Be sure to ask which of their select 16 ounces are on special that day and keep the hops coming long after happy hour.

Don’t worry about showing up hungry. Surrounding food trucks offer moderately-priced bites like ahi sliders, Asian dumplings, shrimp and $1 oysters as well. In addition, guests are also welcome to walk over and bring food back from the neighboring Bartlett Farm.

The Pearl & The Boarding House

The pearl nantucket island

Those looking for a chance to dress up can indulge in modern translations of exotic coastal flavors in a classy, exotic happy hour. The Pearl is island sophistication at its finest, receiving many awards such as The Best Seafood Restaurant in all of New England by New England Travel & Life.

Due to the intimate fine dining atmosphere, the recommended dining age at The Pearl 10+. Bring your date or best friends for an afternoon of upscale seafood with an Asian twist. Share small plates and toast to new adventures over classic cocktails. Read more about their featured menu in this full review of the restaurant.

After a few drinks, consider heading downstairs to The Boarding House, another venue with the same owners. With a cellar dining room and outdoor patio, this space offers a more relaxed scene, award-winning wine, and seasonal dishes.

Brotherhood of Thieves

The brotherhood of thieves nantucket

Mingle with the locals at Brotherhood of Thieves. The bar’s rustic interior design, outdoor gardens, and local brews make it a popular afternoon watering hole. In fact, this 1840’s inspired whaling bar has been an island tradition since it opened its doors nearly 50 years ago.

On a warm summer day, sit out on their patio, surrounded by shaded awnings and hops plants. With an outdoor Rhum bar, spirits will not be in short supply. Try their Paper Plane, described as a “soft gliding cocktail” or their Daffy Martini, made with Grey Goose, lemon, Prosecco, thyme and a twist.

Brotherhood of Thieves’ also offers happy hour specials— including generously portioned $5 bar appetizers made with organic ingredients and on-special drafts— as a casual prelude into the night.


Millies restaurant nantucket

Although they offer no formal happy hour menu, crowds come to Millie’s any way for their specialty drinks served in mason jars, like their local Madaket Mystery, and light appetizers, including their ginger and soy marinated tuna.

It’s easy to extend happy hour into the late evening here, or even just until the sunset for the stunning view— best seen from upstairs. Curious to learn more about the atmosphere and food at Millie’s? Read our restaurant review or check out their menu.

The Club Car

The club car nantucket

Get ready for a one-of-a-kind experience. The Club Car is exactly what it sounds like, a brightly-lit converted train car splashed with modern vintage elegance. Their live piano music pairs with a variety of food, craft cocktails, and drinks, attracting crowds from all across the island for afternoon entertainment and drinks. Try their Bee’s Knees with gin, ginger honey, lemon, orange bitters, and falernum or a seasonal Day Trippah with coconut, pineapple rum, and other exotic flavors.

Featuring healthy tapas, toasts and small plates, The Club Car is the perfect place to share lite bites or even delve into a full dinner menu. With a chef who specializes in gluten-free cuisine, The Club Car is ideal for those with special dietary needs. Even some desserts are safe game.

Happy Hour Doesn’t End There

These are just a select few of the many options for celebrating happy hour on Nantucket but there are lots more. Brant Point Grill, Galley Beach, American Seasons, Ventuno, Lola 41, Cru, The Summerhouse and The Gazebo— the list goes on.

Continue your search for island hotspots with our help. Download our Restaurant Guide to explore all Nantucket's best scenes and choose your must-stop spots.

Nantucket Restaurant Guide


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Stephen Maury

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