If you’ve never heard of Shelter Island, you’re not alone. (Or maybe you have heard of it — in the news, when Scott Disick was kicked out of its Sunset Beach hotel last summer.) This gorgeous island is the Hamptons for people who don’t like the Hamptons, proving that you don’t need to be in Montauk to have a good time. Plus, you don’t need a car: Take the North Ferry from Greenport (service stops at midnight) or the South Ferry from North Haven, also known as Sag Harbor (this service runs until 2am for all of you night owls).
So why not enjoy some laid-back cocktails on the waterfront and spend your days exploring idyllic forests and beaches? Read on for your guide to Shelter Island, and may you find shelter from the storm — of massive crowds descending on nearby overdone hot spots.
Places to Stay
Gimme shelter — at Shelter Island House, preferably. The aptly named hotel is perfect for a weekend trip spent by the pool if your goal is to just kick back and relax. Sunset Beach (a serious Shelter go-to, which you’ll soon figure out if you haven’t already) offers luxurious accommodations as well as an active nightlife scene.
Other waterfront options include the Ram’s Head Inn and The Pridwin — at the latter, you can book either a hotel room or an entire cottage for yourself (some even have views of the bay). If you prefer to be directly in town, check out The Chequit: Its single rooms and suites are a walkable distance from the ferry, making it a great staging ground for car-free vacationing.
Where to Eat and Drink
Sunset Beach’s restaurant is a splash of Saint-Tropez on the east coast of New York. Its infinitely Instagrammable yellow-striped décor is best captured at (you guessed it) sunset, but if you head there earlier for some swimming time you’ll be sure to enjoy a leisurely day well-spent. Definitely the most Hamptons-esque spot on the island, this bar/restaurant/hotel always has a great DJ, and the food is the best on the island. Late night is perfect for drinks around the firepit out back.
SALT Waterfront Bar & Grill is situated at an ideal location in the Shelter Island boatyard — people can even call ahead at the Island Boatyard to moor their craft and grab lunch or dinner. A few steps away, the Shipwreck Boat Bar is built into an old twin-mast hull (you have to see it to believe it), and patrons often enjoy beanbag toss games between cocktails. Shelter Island Craft Brewery makes for a fun day trip: They brew their own beer right on the island.
Opened just last summer, the Italian restaurant and bar Isola is a strong addition to the Shelter Island scene. The kitchen stays open late, which is perfect for stragglers coming off the ferry. And its food is phenomenal — particularly the Neapolitan-influenced pizzas — with most of the ingredients sourced locally. Isola is perfect for a big group dinner or a casual drink or meal at the bar. If you’re feeling fancy, head to either 18 Bay or Vine Street Café for a sophisticated dinner out. Traveler’s tip: At Vine Street, order the insanely good Bolognese.
For breakfast, head to Stars Café (if you get a late start, this cute coffee shop is open for lunch as well). Marie Eiffel Market boasts the world’s best crab cake sandwich (an unofficial title bestowed by me, but trust me), so pick up a couple before heading to the beach. When you’re ready for a break, stop by Tuck Shop for a waffle cone.
What to Do
This underrated island retreat is home to significant spaces of undeveloped land. Find yourself in nature in the Mashomack Preserve and embark on a hiking trail: The preserve accounts for one-third of the island. Or check out Sylvestor Manor — a 17th-century estate owned by the same family for 11 generations, who originally enslaved people to support their West Indies sugar plantations — which was recently restored as a working educational farm. Visit their farm stand in the summertime to sample some local produce (they’re also a primary supplier for Isola), or take a tour of the historic property to learn more about the estate’s history. The manor also hosts concerts, dances, and plays, so keep an eye on the schedule if you feel like taking in some culture.
Would it be an island vacation if you never visited the shore? While most of Shelter Island’s beaches require a permit to park a car, if you’re not a local and don’t want to spring for the fee, you can either rent a bike at Piccozzi’s Bike Shop or make a lunch reservation at Sunset Beach to spend time at Crescent Beach (located directly across the street). There are paddle boards and kayaks available at Crescent Beach — as well as beach massages for the less outdoorsy among us. If you’re looking to get your fitness on, definitely visit Shelter Island Yoga & Fitness at the Derring Harbor Inn. They have daily classes like yoga, spinning, and Pilates, as well as tennis courts you can reserve for a match and an off-site barre studio.
Looking to spend some time shopping? Your first stop should be Dabney Lee, where you can find sundresses and beachy accessories like wine thermoses, games, and floaties. This is also the perfect place for a hostess gift if you’re spending the weekend as a guest. Stock up on fluffy beach reads at Finley’s Fiction, which focuses on recent releases, or more serious literary picks at Black Cat Books, which sells vintage, rare, and other fine used books.
Finally, for some good old Americana, go check out a baseball game. The Shelter Island Bucks are part of the Hamptons Collegiate Baseball League, a Long Island summer league that plays at the local high school. Maybe pick up an ice cream on your way there for a real throwback weekend.
Where do you like to go when you leave your car behind? Let us know @BritandCo!
(Photos via Getty)
