Your Next Weekend Escape: Nantucket

While you can reach the island by ferry from Cape Cod, the fastest way to the summer getaway is by plane. JetBlue offers a seasonal nonstop from JFK that takes just over an hour (we spotted one-way fares as low as $78 in August). For baller status, charter a plane from Tradewind Aviation, which now offers a shuttle route from New York City. Perks include free checked bags, snacks, drinks and a flexible booking model for the cost of a single seat.

Nantucket has no shortage of quaint accommodations, but two that stand out include the wildly popular White Elephant and the stylish 76 Main. Located on the waterfront, the nautical-inspired White Elephant hotel offers stunning panoramas (including views of the Brant Point Lighthouse), light-filled guest rooms and a lawn overlooking the harbor (an ideal spot to sit and sip rosé). At 76 Main, the interior design takes a more contemporary turn, with bold patterns and nods to the history of New England. Plus, the boutique hotel is mere steps from the shops and restaurants of the island’s main drag.

Kick off the weekend with a visit to Cisco Brewers, where you can sample seasonal and classic beers while listening to live music and noshing on bites from local food trucks. Nearby is also Triple Eight Distillery, which makes fruit-infused vodkas and liqueurs in flavors like pineapple-jalapeño and ginger-honey. For a classic oyster feast, drop into Cru: It feels like you fell into a Ralph Lauren ad—the fashion designer did the interiors—and it’s located right on the docks for prime people watching. On Sunday, plan on a massive brunch at Brant Point Grill, inside the White Elephant, where the epic lobster Bloody Mary features a whopping quarter-pound of lobster.

Take advantage of Nantucket’s water, whether that means chartering a boat for a day of sailing or spending time on the sand at one of the many picturesque beaches. The best way to get around is via bicycle: If you’re staying at the White Elephant, grab one of the bikes available to guests, or you can rent some wheels from the Nantucket Bike Shop (which has scooters too). Learn about the island’s roots as a fishing destination for Native Americans at the Whaling Museum, and for something more interactive, sign up for a cooking class at the relatively new Nantucket Culinary Center. The courses, geared toward adults or children, focus on sustainable dishes using the island’s local ingredients. That includes everything from freshly sourced shellfish to local purveyors’ specialty products.

The now-iconic Nantucket Reds (those ubiquitous preppy pink chinos) were made famous by island staple Murray’s Toggery Shop, which also houses a selection of beach-ready goods and gifts. Beauty hounds should stop by Follain, the all-natural skin-care shop founded by Nantucket regular Tara Foley. She stocks products from 75 different brands, all focused on clean beauty. On Saturdays, swing by the Sustainable Nantucket Farmers and Artisans Market on Cambridge and North Union streets, where everything for sale is grown or produced on the island.