Shelter Island sits between the lively Hamptons and the increasingly popular North Fork, offering the best of both. It’s not as hidden or exclusive as it used to be, but it still feels like the Hamptons’ quieter relative—partly because you can only reach it by ferry. In recent years, though, the island has welcomed a wave of new restaurants and hotels, many of which are still refreshingly less crowded than their mainland counterparts.

Even though you can drive across the island in under 30 minutes, there’s a surprising variety of places to stay and things to do. The hotels range from Americana-style resorts to cozy bed-and-breakfasts, while the dining scene has become so good that people come from the mainland just to get a table. Still, the island keeps a sense of being untouched and unspoiled, especially when you wander through a quiet nature preserve or along a rocky beach.

For anyone wanting a taste of the “out East” vibe without the Hamptons’ crowds and high prices, Shelter Island is a stylish, line-free escape. Use this guide as a starting point for discovering what’s new and what’s classic on this little gem of a vacation spot.

Where to Stay

The Boathouse by Boutique Homes
Photo: Courtesy of The Boathouse by Boutique Homes

Just a short walk from the North Ferry, The Boathouse is the perfect base for anyone wanting to pretend they own a Shelter Island home for the weekend. This new rental from Boutique Homes has 3 bedrooms and 3.5 bathrooms, and it was furnished in partnership with Design Within Reach—almost everything inside can be bought. It’s a private retreat that blends Scandinavian design with a California coastal feel, plus plenty of Long Island charm. You’ll enjoy harbor views and sailboats right outside the window, and the large yard with an outdoor kitchen is ideal for relaxing and hosting. There’s also a hot tub and sauna, perfect for a fall getaway out East.

The Pridwin Hotel
Photo: Courtesy of The Pridwin Hotel

Built in the 1920s, this hotel feels like it stepped out of a Norman Rockwell painting. After a full restoration and renovation in 2022, the property got a fresh update, including its 33 rooms and 16 private cottages. Sitting right on sandy Crescent Beach, this family-friendly spot has a swimming pool, tennis court, and bikes you can borrow, giving it a fun summer-camp vibe. Highlights include the hotel bar, where the cocktail menu is put together by NYC’s Dante team (tip: grab a porch seat for evening drinks and a stunning sunset), and their Wednesday night summer BBQs—a classic cookout right on the water.

The Chequit Hotel

A true boutique hotel on the island, the Chequit has airy, coastal-style rooms with water views in Shelter Heights. It’s within walking distance of cafes and shops, making it a great home base for a weekend of exploring. This season, there’s a new in-house restaurant serving Italian dishes with a coastal twist. There’s also an on-site cafe where you can grab coffee and a pastry to enjoy from the wraparound porch. It’s close to the North Ferry too, if you want to hop over to Greenport for an easy dinner. The hotel group also owns a classic 1926 sailboat that can be chartered for trips and special occasions right from Shelter Island.

Sevens Shelter Island

A bed-and-breakfast that feels more like a home, Sevens has seven private king rooms decorated in a simple, modern style. Your stay includes access to a large heated pool and a daily European-style breakfast set up in the kitchen, featuring local cheese and provisions. Bring a big group and you can book the whole place.

Where to Eat

The dining room at Léon 1909.
Photo: Greg Kessler

Vine Street Café and Market

Serving the island for over 20 years, Vine Street is a laid-back bistro and a trusted favorite among locals and visitors. The menu leans heavily on produce from local farmers and fishermen. Always check the daily specials, like the M…Monday evening bouillabaisse. They’re open all year, which is rare on the island, so locals really rely on them. Around the back, there’s a small market selling basics like cheese and crackers, plus their own sauces, including mignonette and tomato sauce.

Sunset Beach
This spot, inspired by the French Riviera and run by hotelier André Balazs, serves coastal French and Italian dishes. You can get there by car or boat, and it’s probably the only place on the island where people go to see and be seen. The restaurant is part of a 20-room hotel and is open every day except Tuesday for lunch and dinner. Late into the evening, a DJ plays by the fire pits and the bar stays busy. Standout menu items include tuna tartare, whole artichoke, and a frozen drink called a frozé on hot days.

Marie Eiffel Market
This café and market is a go-to for breakfast and lunch, especially for grab-and-go items like pre-made salads and frozen foods. It’s a great place to stock up for the weekend, with fresh pastries and coffee every morning, plus lunch sandwich specials like a lobster roll.

Léon 1909
Léon 1909 is still one of the hardest reservations to get in summer, whether you live on the island or are just visiting. This French-Italian restaurant is built around an open hearth, which makes the space feel cozy and gives the food a nice smoky finish. With a modern farmhouse look, the menu features homemade breads made from local grains, seasonal seafood like Montauk red shrimp crudo, and fire-roasted favorites such as a tasty burger and a slow-roasted half chicken. The cocktails are precise and creative, with unique infusions and modern twists on classics. (Even though the desserts are great, locals know to head across the street to the Tuck Shop for a sweet treat that really captures summer.)

Opties and Dinghies
In the middle of the island, Opties and Dinghies is an unexpected find. A husband-and-wife team runs it, offering a handwritten chalkboard menu that mixes Chinese and French dishes like fresh dumplings, homemade pastries, and crepes. From kimchi salad to giant scallion pancakes, plus both savory and sweet crepes, there’s something for everyone. Open daily until 9 p.m., they also serve gelato from Il Laboratorio del Gelato. (Tip: They also sell frozen dumplings to take home.)

Blue Han
New this summer, Blue Han is a Korean kitchen and café with classics like tteokbokki and seafood and green onion pancakes. They also offer signature trays with a variety of banchan, plus bigger dishes like bibimbap and different kinds of kimbap. It’s sure to become a favorite on the island, offering something different from the usual coastal European food.

Peeko Oysters
Don’t be put off! You can preorder and pick up a bag of ready-to-shuck East End oysters from the simple Peeko’s stand.

King Andrew Cheese
This cheese wagon on the island is a treasure trove of specialty cheeses from around the world. With breads and spreads to round out the perfect cheeseboard, King Andrew Cheese will give you sample after sample to make sure you find the right wedge for any occasion. Hours vary, but they have a self-service fridge stocked with cheese, so you can still grab some even when the barrel-shaped cart is closed.

What to Do
A creek at Mashomack Preserve.
Photo: Sylvie Florman

Mashomack Preserve
Spanning over 2,000 acres, Mashomack is a pristine and special nature preserve right on the island. With walking trails from half-mile loops to longer routes with sweeping water views, you’ll see plenty of birds and wildlife, including the occasional fox.

Sylvester Manor
A charming, historic working farm on the island, Sylvester Manor has a small store selling homegrown produce, various baked goods, and provisions from the North Fork. Surrounded by fields of vegetables and flowers, you can explore walking trails across their 200-plus acres, which feature a seasonal sculpture show set in nature.

SPRMRKT
Inside the island’s only grocery store, a humble but well-stockedIGA is SPRMRKT, a streetwear shop with an island theme, inspired by the supermarket where it’s located. It was founded by Anthony Peronace, who grew up stocking shelves at his parents’ market. Their products draw on the Shelter Island setting and classic supermarket imagery, creating unique, one-of-a-kind souvenirs. Everything is designed and made on Shelter Island, and some items are even packaged to look like meat from a butcher counter, complete with styrofoam trays and plastic wrap.

Shop Shelter Island Heights
You can’t really call any part of Shelter Island “downtown,” but Shelter Island Heights is the closest you’ll get. For a cluster of shops within walking distance, you’ll find coastal-themed home goods and fashion accessories, including women’s clothing boutiques like Purethread and Pure Soul Boutique. Just up the street, the small but well-curated Finley’s Fiction is great for new releases, in case you forgot to bring a book for the beach.

Black Cat Books
A haven for used books for 30 years, if you’re willing to do a bit of searching, you can uncover plenty of collectible titles and hidden gems.

Frequently Asked Questions
Here is a list of FAQs about Shelter Island designed to answer both basic and more nuanced questions for firsttime visitors and seasoned Hamptonsgoers alike

General Planning

Q Where exactly is Shelter Island and how do I get there
A Its a small island nestled between the North and South Forks of Long Island right where the Peconic Bay meets Gardiners Bay You can only get there by ferry You take a 10minute ferry from Greenport or a 5minute ferry from North Haven

Q Is Shelter Island actually part of the Hamptons
A Not technically The Hamptons are on the South Fork of Long Island Shelter Island is a separate town in its own right but its often grouped with the Hamptons because its a quick ferry ride away and shares a similar upscale beachy vibeminus the crowds

Q When is the best time of year to visit
A For the full experience visit between Memorial Day and Labor Day For a quieter more peaceful visit with cooler weather and stunning fall foliage September and October are perfect Many businesses close during the winter

Q Do I need a car on Shelter Island
A It helps but its not necessary The island is only about 12 square miles and many people bring bikes You can rent a golf cart which is a popular and fun way to get around There is also a local jitney service during the summer

Where to Stay

Q What kind of accommodations are available Are there big chain hotels
A You wont find any chain hotels The island is known for charming historic bedandbreakfasts boutique inns and private house rentals The Pridwin is a classic waterfront hotel and there are many luxury vacation rentals available through local agencies

Q Is it better to stay on Shelter Island or in the Hamptons and just visit for the day