“Hearst Magazines and Yahoo may earn commission or revenue on some items through these links.”
If you’re hoping to travel locally for a quick summer getaway, I’d strongly recommend Shelter Island. Located 90 miles east of New York City between the North and South Forks of Long Island, the town originally known as Manhansack-aha-quash-awamock (translation: “an island sheltered by islands”) specializes in laid-back luxury, so it’s not surprising that everyone from Christie Brinkley to Kendall Jenner have paid a visit. Take the LIRR north to Greenport, hop a ferry, and soon you’ll be surrounded by water and feel instantly at ease. Whether you enjoy biking, shopping, or just laying out at the beach with a good book, there’s something for everyone here.
What to See
Crescent Beach
Accessible via ferry and named for its crescent shape, this beach is a popular option, thanks in large part to parking spaces, bathrooms, lifeguards, a food truck, and unbeatable views of Greenport. Get your camera ready for sunset, too.
Marika’s
Shelter Island and Marika’s go hand-in-hand, along with owner Marika Kassik’s penchant for vintage homewares and real estate. The Sotheby’s agent, celebrating 40 years in business, has been furnishing and cleaning out homes on the island for decades—just check out her impressive hauls on Instagram.
Dan’s Bike Rental
Take it from a skeptic: cycling is one of the best ways to see Shelter Island. If you don’t have a bike, text or call Dan’s Bike Rentals and get one delivered anywhere between Mattituck and Orient Point on the North Fork, including the LIRR station and Orient Point Ferry.
Princess Cropped Blouse
$120.00 at frankiesbikinis.com
Kaylee High Rise Pinched Loose Shorts
$138.00 at pistoladenim.com
Malta Handwoven Straw Tote
$115.99 at jcrew.com
Where to Eat
Léon 1909
No matter what you order, you can’t go wrong at Léon 1909. Though located inland, the restaurant offers seaside French-Italian food made with local ingredients, ranging from the expected (the burger and grilled pork chop) to the unexpectedly delicious (don’t miss the melon and french bean appetizer). And, even though it costs $3 extra, the housemade bread and cultured butter is well worth it—trust me.
The Terrace
Whether you’re staying at The Pridwin or just passing through, its water-view restaurant and bar, The Terrace—overlooking Crescent Beach—is a great option. Just ask designers Marina Larroudé and Alejandra Alonso Rojas, who count it among their regular spots. The menu features classic Long Island fare like char-grilled Atlantic oysters and crab cakes along with a long list of fun summer cocktails.
Stars Café
Locals love the family-owned Stars Café for its freshly baked goods, coffee, breakfast burritos, burgers, and juice and smoothie bar…so basically everything you could ever want.
Sonny Top
$158.00 at withjean.com
Linen Simple Pant
$168.00 at shopdonni.com
Elba Lariat Belt Chain
$188.00 at nottejewelry.com
Where to Drink
Sunset Beach
Come for the drinks, stay for the sunset and celeb clientele at this André Balazs-owned boutique hotel across the street from Crescent Beach. It draws a fashion crowd not only for the picturesque location but also for its exclusive pop-ups featuring brands like Giorgio Armani Mare.
SALT Waterfront Bar & Grill
Set along West Neck Harbor on the southern side of the island, SALT is a low-key waterfront favorite known for its great cocktails, sunset views, live music, and the kind of effortlessly cool charm that makes it feel like a well-kept secret.
Shelter Island Craft Brewery
Shelter Island Craft Brewery calls itself “a craft brewery located on your favorite little island,” and it delivers on the vibe with local favorites like Peach Beach Summer Ale and even rosé on tap. Need we say more?
June Nap Top
$118.00 at hillhousehome.com
Delphine Nap Skirt
$150.00 at hillhousehome.com
Amanu Sandal
$395.00 at alcltd.com
Where to Stay
The Pridwin
The Pridwin is like adult summer camp—in the best possible way. Think: campfires, water sports, pickleball, guided hikes, sunset cocktails…the list goes on. Originally built in 1927, the hotel underwent a renovation a few years ago by Cape Resorts and The Petry family that’s equal parts cozy and modern, complete with luxury amenities like a waterfront spa. This summer, clean beauty brand ONDA and L.A.-based lifestyle label Sporty & Rich are both popping up on-site through Labor Day. The former is hosting a seasonal residency in the treatment rooms, offering facials and a curated selection of shoppable products. Meanwhile, Sporty & Rich is taking over The Pridwin’s tennis courts with wellness programming that includes tennis clinics and Forma Pilates sessions.
The Rams Head Inn
Situated on the top of a hill across 4.5 acres of land, The Rams Head Inn boasts its own private beach with surprisingly comfortable day beds, 17 rooms, a restaurant, a bar, and an event space that’s practically made for weddings.
The Chequit
The Chequit, which dates back to the 19th century, is a hotel and restaurant in the center of town with country-chic rooms, complimentary breakfast, and a pantry stocked with snacks.
Billiards Tee
$75.00 at fwrd.com
Mini Track Short
at eterne.com
Outta Love Sunglasses
at revolve.com
Beauty Picks
Ultra-Lightweight Face Fluid SPF 30
In terms of sunscreens, it doesn’t get much better than this lightweight formula that glides on smoothly without feeling greasy or leaving behind a white cast. Apply it liberally to your face each morning, then reapply every two hours.
$19.99 at ulta.com
Wave Spray
Embrace salty beach hair with this cult-favorite wave spray—it’ll help you achieve that effortlessly undone texture and replace the smell of the ocean with fresh florals.
$30.00 at sephora.com
Lip Butter Balm
Summer is the perfect time to be makeup-free, but if you want a touch of natural-looking color, try a swipe of this moisturizing vegan balm.
$24.00 at sephora.com
You Might Also Like
-
The 15 Best Organic And Clean Shampoos For Any And All Hair Types
-
100 Gifts That Are $50 Or Under (And Look Way More Expensive Than They Actually Are)
