This Secluded New England Island Is the Dreamiest End-of-Summer Escape — Full of Lobster Rolls, Stargazing, & Rosé on the Water

Not ready to say goodbye to summer just yet? Well this storybook island off the coast of Massachusetts might be your perfect last hurrah of a weekend getaway. With cobblestone streets, wind-whipped beaches, and some of the most charming stays in New England, Nantucket is a dreamy end-of-summer escape that feels worlds away from NYC — but is totally doable for a long weekend. And while it may be known for its preppy charm and quiet exclusivity, it’s quietly becoming one of the East Coast’s most sought after travel destinations —perfect for food lovers, stargazers, and anyone craving that nostalgic, salty breeze before fall sets in. Sail, bike, and stargaze your way through August & September ------------------------------------------------------------ There’s still time to soak in the island’s signature pleasures — like chartering The Blue Peter , a classic 1930s teak sailing yacht, for a sunset or lunch sail through September, complete with lobster rolls and chilled rosé on deck. You can also explore the coastline on two wheels — rent a bike and take the scenic path out to Surfside Beach , or ride the Polpis Trail past cranberry bogs and salt marshes. Don’t miss the Sconset Bluff Walk , a quiet footpath behind seaside cottages with Atlantic views that look straight out of a Nancy Meyers movie. For a slower pace, curl up with a book in the island’s historic Atheneum Library , or catch a clear night at the Loines Observatory , where the Maria Mitchell Association hosts stargazing events through early fall. Where to stay: boutique hotels & beachy retreats ------------------------------------------------ In the heart of downtown Nantucket, check into Greydon House — a boutique 20-room hotel designed by Roman and Williams. The interiors nod to the island’s maritime history with richly layered details, hand-painted Portuguese tiled showers, and plush custom beds that practically demand an afternoon nap. Right next door, the new Cisco Surf Suites offer a more casual, apartment-style experience — think spacious three-bedroom layouts with vaulted ceilings, full kitchens, and the option to combine units into a six-bedroom setup. It’s ideal for families or friend groups looking to linger. Where to eat (besides lobster rolls & rosé) ------------------------------------------- In between all of the shopping and activities you may be doing in Nantucket, you’ve got to fuel up! These are our handpicked spots of the town’s dining scene that you need to highlight on your itinerary: * Cru : A glam waterfront oyster bar perfect for watching the boats with a glass of champagne in hand. * Galley Beach : Beachside dining at its finest — sunset views, elevated coastal fare, and toes in the sand. * The Club Car : Housed in a vintage train car, this lively spot is a favorite for cocktails, piano music, and late-night bites. * Ventuno : A candle-lit house-turned-restaurant that feels like a dinner party with rustic Italian fare. * Cisco Brewers : The ultimate laid-back hangout, with live music, food trucks, craft beer, spirits, and hard seltzers all in one breezy outdoor space. * The Gazebo : An iconic open-air bar in the heart of town known for its legendary mudslides. * The Juice Bar : A must-stop for homemade ice cream and waffle cones rolled right in front of you. How to best get to Nantucket from NYC ------------------------------------- Ready for your big trip? There’s plenty of ways to get there from NYC. Nantucket is about a 5 hour drive from NYC , or you can take a train or bus to the area before taking the ferry across the water to Nantucket . Alongside normal transportation, Seastreak even runs a high-speed ferry service from East 35th St., Manhattan or Highlands, NJ, direct to Nantucket (with a quick stop at Martha’s Vineyard) during select weekends and summer dates. It’s the only ferry service that runs direct from NYC to Nantucket , and seats sell out. Or for the very fastest option of all, fly direct from NYC into Nantucket Memorial Airport via JFK or LGA — flights are short (around 1 – 1.5 hours) and surprisingly scenic. Source: https://secretnyc.co/nantucket-massachusetts/