If you’re in Massachusetts, Nantucket included, you’re eating seafood for dinner. The oysters at Cru (open for the season from May) are well-known; book far ahead and order some Champagne to pair with the bivalves on the waterfront. For something more upscale, head to nearby Dune for Atlantic halibut with coconut-lemongrass broth and chili-rubbed shrimp tostadas. An old-fashioned Nantucket clambake—replete with the essentials like steamers, mussels, clam chowder, lobster, corn on the cob, potatoes, butter, and broth—awaits at Sayle’s Seafood starting at $42 per person. The bake can be made to-go or catered; add-ons include shrimp cocktail, oysters on the half shell, and cheese platters.
For ice cream—a food group in which Massachusetts excels—Juice Bar is a classic for an oversized scoop of chocolate Oreo ice cream in a fresh, buttery waffle cone. There’s usually a line outside, but don’t let it deter you—it moves fast, and you’ll need the wait to choose among the dozens of flavors.
While there’s too much good food on the island to possibly name, you can also consider charcuterie plate at the Proprietors, margaritas in Madaket at Millie’s, and peanut-crusted halibut at Sconset Café.
Courtesy Life House Hotels
Where to stay in Nantucket
The Faraway
Featured on Condé Nast Traveler’s 2022 Hot List, the Faraway is one of the hippest hotels on the island—but you feel the age-old spirit of Nantucket on the property, too. We also love the glossy new bikes on loan that you can pedal straight to Steps Beach (or further). The 58 rooms are nestled in four historic houses downtown. The Faraway’s bar and restaurant, Sister Ship, is one of the hottest places in town to grab cocktails—they’re famously good—and is a scene unto itself. Executive editor Erin Florio sets the scene: “The bar recalls 1920s glamor spots in Paris with its vintage lamps and brass shelves, while the restaurant is a mash-up of thoughtfully designed spaces.” —From $850 per night
The Nantucket Hotel
While the hotel landscape on Nantucket is distinguished by plenty of posh stays and bed-and-breakfasts alike, The Nantucket Hotel bills itself as the island’s only year-round stay. It sits inside a shingle mansion with a spacious wraparound porch, and has a past life as the 1891 Point Breeze hotel. Besides the hotel’s history, its homemade popovers, plush bathrobes, and complimentary ferry pick-up and drop-off service contribute to a feeling of home. Though the two outdoor swimming pools are unlike home for most. —From $620 per night
Historic home with gorgeous interiors
Hosted and renovated by an interior designer, this six-bedroom house is located on the edge of Nantucket’s well-preserved historic district, and is a 10-minute walk from town. The furniture, art, and design in this space, dotted with elegant midcentury touches, are truly a marvel. Ideal for a family seeking a vacation rental with style, the charming backyard and patio, bordered by the island’s classic hydrangea bushes, is the perfect setting for coffee, a cookout, or a drink after the beach. On top of all that, it has a solid 5.0 rating on Airbnb. —From $900 per night
Two-bedroom beachfront cottage in Madaket
A true waterfront property, directly across the street from the beach, this total gem in Madaket would be perfect for a small family looking to spend all day on the sand. The deck looks out over the Atlantic Ocean, the perfect place to relax while taking in the sunset. Inside, you’ll find beautiful hardwood floors, warm knotty pine, and classic coastal furniture. —From $750 per night
The White Elephant
A seven-time Readers’ Choice Awards favorite and a Gold List winner in 2024, The White Elephant is a luxe waterfront resort with a hotel, inn, several cottages, and a couple loft options, all a short walk from downtown. It’s an excellent choice for families or groups of friends who want a space of their own, and thoughtful design touches with a view of the ocean from Brant Point. —From $325 per night
The Wauwinet
A Relais & Chateaux hotel, and sister property to the White Elephant, the Wauwinet is Nantucket’s grande dame. Located on the more remote, northeastern tip of the island, the Wauwinet attracts couples or families content to be in a quiet area. It’s at once fancy and romantic. —From $525 per night
