The 100-square-mile home of ship captains, celebrities, and everyone in between, this rich and varied New England island has farms, beaches, and the world's cutest gingerbread houses.
A recent trio of design-conscious small hotels has lit up the Vineyard's slumber scene like a beach bonfire. The Sydney, a refreshed 1892 ship captain's home, and The Christopher, a veritable lollipop of Caribbean color and design inside an elegant Victorian, both hold court in the village of Edgartown. In nearby Oak Bluffs, Summercamp has taken over the historic Wesley Hotel on the waterfront with playful interior design, nouveau-camp spaces including an AstroTurf Rec Hall, and a long porch lined with sea-facing rocking chairs.
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In Oak Bluffs, 20byNine is a whiskey-forward cocktail spot (and the home to Sunday's best brunch); its sister restaurant, Down Island, offers a five-course meal based on what's local and fresh. (The menu changes weekly.) Don't miss Vineyard locals' only choice for late-night cravings: Back Door Donuts. Normally low-key Vineyard Haven just took a step into the spotlight with the arrival of Garde East. The sophisticated waterfront eatery views local seafood through a creatively French culinary lens.
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There's more than just sweet grabs and savory sit-downs at Rosewater Market and Take-Away in Edgartown. The sunlit space is stocked by mercantile angels—curated cookout needs, cocktail-party ephemera, serenely beautiful pottery, and notes and cards to send glowing reports back to the mainland. The swag of the summer is prep-forward accessories from Chappy Happy (available at Rosewater Market, as well as Crossroads Gallery in Oak Bluffs).
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Join MV-savvy locals and tourists alike who make it a summer rite of passage to jump from the small span between Edgartown and Oak Bluffs known as the "Jaws Bridge."
Photo: Courtesy of Massachusetts Office of Tourism/M. Bossman