Photo: Chris Hackett/Getty Images

Just far enough off the Massachusetts coast to feel remote (and exclusive), this faraway island blends urbanity and escapism in perfect balance.

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Name your poison: for nostalgic resort pleasures wrapped in updated, elegant style (including a charming pool and wraparound porch), the Nantucket Hotel & Resort has gifts in spades, plus a divine vacation package that pairs a stay here with one at its sister property on Martha's Vineyard. For a graceful historic aesthetic, the recently renovated Roberts Collection has three 19th-century homes (and one built in 2013 that fits right in) around a lush, brick courtyard. (The latest update, at Roberts House, features vibrantly contemporary interiors.)

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The sailor's life is one buoyed by the late-day cocktail, and bars are therefore central to the daily rhythms here. For the smartest crafted pours, settle in at the fairy-tale tavern–style bar at Greydon House, an intimate luxury hotel in a historic home (and home also to a tiny, knockout restaurant). Nearby, The Nautilus teams an excellent bar menu with a parade of delicious small plates; the bar remains a buzzy locus of locals hanging out.

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 If Nantucket had an official sport, it might be hunting and gathering—of the boutique variety. Stop one needs to be Skinny Dip Nantucket, the superb, nautically inspired collective of women's, men's, and lifestyle brands, including the designer-owners' own Beau & Ro Bag Company, and Ellsworth and Ivey. (Prepare to be knocked out by N.TUC's obsessively cravable clothing and pillows with Nantucket-inspired graphics.) Two Boston-based boutiques have must-visit Nantucket outposts: The bright, whitewashed space at Follain, the intimate beauty emporium with a wholesome mission of all-natural products, provisions clean living (and your summer beauty routine). Meanwhile, Crane & Lion offers up a gorgeous line of clothing for the yoga-fueled, workout-tinged lifestyle known prosaically as "athleisure."

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Photographer and homegrown talent Michael Gaillard's large-scale works inject real meaning into the word "breathtaking." Visit his eponymous gallery to see why. Artist Lee Milazzo's Samuel Owen Gallery (with footprints on Nantucket and in Greenwich, Connecticut) has an eye-popping collection of contemporary art, including works by Damien Hirst and Shepard Fairey.

Photo: Chris Hackett/Getty Images