The Best Hotels, Beaches, and Restaurants
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 laidback 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 has furnished and cleaned out homes on the island for over 30 years—just look at her 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.
Beyond Yoga x Donni Terry Bralette
Now 50% Off
Beyond Yoga x Donni Terry Henley Short
Now 50% Off
Teva Flatform Universal Sandals
Now 60% Off
Where to Eat
Léon 1909
No matter what you order, you can’t go wrong at Léon 1909. 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. 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.
Hill House Home The Eyelet Dottie Nap Dress
Now 60% Off
Mejuri Charlotte Bold Hoops
Saint Laurent Tribute Nu Pieds Slide Sandal
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 its pop-ups with the likes of Marni.
The Flying Goat
Golfers, take note: This no-frills bar and restaurant at the historic Shelter Island Country Club, a.k.a. “Goat Hill,” has cold drinks and a vantage point that’s one of the highest on the island.
White Oak Wine Garden
In the mood for wine? Look no further than White Oak Wine Garden. The tasting room serves rosés and boutique bottles by local winemakers in an outdoor garden with live music.
Mirth Shoreditch Smocked Open Side Top in Petunia
Mirth Mirth Pant in White
Birkenstock Arizona Soft Sandals
Where to Stay
The Pridwin
The Pridwin is like adult summer camp in the best way possible. Think: campfires, watersports, pickleball, guided hikes, sunset cocktails—the list goes on. Originally built in 1927, the hotel recently underwent a renovation by Cape Resorts and The Petry family that’s equal parts cozy and modern, with luxury amenities like a full-service spa. What’s more, French fashion house Balmain has a pop-up of its high summer and pre-fall collections at the property through August 15.
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 ideal for weddings.
The Chequit
Also recently renovated, 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.
Tory Sport Side-Slit Tennis Dress
Lands’ End Medium Natural 5 Pocket Open Top Canvas Tote Bag
Short Court Back in Black Set
Beauty Picks
BYOMA Moisturizing Gel Cream 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.
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.
Summer Fridays 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.
