For those looking to experience a taste of the “out East” without the crowds (and prices) of the Hamptons, Shelter Island is a chic oasis—and most importantly, free of lines.For those looking to experience a taste of the “out East” without the crowds (and prices) of the Hamptons, Shelter Island is a chic oasis—and most importantly, free of lines.
Between the bustling Hamptons and the increasingly popular North Fork sits Shelter Island, a perfect combination of the two. No longer as secluded or secret as it once was, Shelter Island remains the Hamptons’ quiet cousin, partially due to its lack of accessibility—you have to take a ferry to get on and off the island. Still, over the last few years, the area has seen an exciting influx of restaurants and hotels, many of which are still blissfully less crowded than their mainland counterparts.
For an island you can drive across in less than 30 minutes, there’s an impressive diversity of accommodations and activities. The handful of hotels range from Americana-inspired resorts to small B&Bs, while the restaurants have gotten so good that visitors are traveling from the mainland just to get a seat. Even so, there’s still an air of the untouched and untainted on the island, especially as you wander through a quiet nature preserve or along a rocky beach.
Built in the 1920s, the hotel is close to a real-life Rockwell painting. Restored and renovated in 2022, the entire property got an update, including its 33 rooms and 16 private cottages. Located right on sandy Crescent Beach, the family-friendly hotel has a swimming pool, tennis court, and bikes for use, giving it a real camp feel. Highlights also include the hotel bar, whose cocktail menu is curated by NYC’s Dante team (pro tip: get a seat on the porch for evening drinks and the perfect sunset view), and their summer Wednesday night BBQs for a classic summer cookout right on the water.
A true boutique hotel on the island, the Chequit offers rooms with an airy coastal feel and views of the water in Shelter Heights. Within walking distance to cafes and shops, it’s a great home base for a weekend of exploring. A new in-house restaurant this season features a menu of Italian dishes with a coastal spin. There’s also an on-site cafe from which you can grab a coffee and a pastry to enjoy with the views from the wraparound porch. It’s also within walking distance to the North Ferry if you want to venture across the water to Greenport for an easy dinner. The hotel group also owns an iconic 1926 sailboat, which can be chartered for trips and special occasions right from Shelter Island.
A B&B that feels more like a home, Sevens has seven private, king rooms decorated in a simple but modern manner. The stay includes access to a large heated pool and a daily Euro-style breakfast set up daily in the kitchen, with local cheese and provisions. Come with a big group and take over the entire spot.
Where to Eat
Serving the island for more than 20 years, Vine Street is a laidback bistro and a reliable favorite among locals and visitors, offering a menu that heavily features produce from local farmers and fishermen. Always check for daily specials, like the Monday evening bouillabaisse. They’re open year-round, a rarity on the island, making them a beloved staple. A small market operates around the back, selling provisions like cheese and crackers, as well as proprietary sauces, including their mignonette and tomato sauces.
Hotelier André Balazs’s French Riviera-inspired hot spot offers a menu inspired by coastal French and Italian flavors. Accessible by car and boat, it’s possibly the only spot on the island where people go to see and be seen. Attached to the 20-room hotel, the restaurant is open every day but Tuesday for lunch and dinner, with a DJ spinning among fire pits and a crowded bar into the late hours. Menu highlights include their tuna tartare, whole artichoke, and frozé on a hot day.
This cafe and market is a particular favorite for breakfast and lunch, with an emphasis on grab-and-go items like premade salads and frozen goods. A good option for stocking your weekend fridge, they also have fresh pastries and coffee each morning, as well as lunch sandwich specials, including a lobster roll.
Léon 1909 remains one of the hottest summer reservations for those on and off the island. The French-Italian restaurant is centered around an open hearth, giving the space intimacy and warmth and the food a unique fire finish. With a modern farmhouse aesthetic, the menu includes homemade breads made with local grains, seasonal seafood dishes like Montauk red shrimp crudo, and fire-roasted mainstays like a delicious burger and a slow-fired half chicken. The cocktail menu is precise and inventive, featuring flavor infusions and mixologist twists on classics. (Despite a delicious dessert menu, those in the know go across the street for dessert at the Tuck Shop, for a real taste of summer.)
Located in the middle of the island, Opties and Dinghies is an unexpected concept, featuring a handwritten chalkboard menu of Chinese and French delights like fresh dumplings, homemade pastries, and crepes from a husband-and-wife duo. With items running from kimchi salad to giant scallion pancakes, as well as savory and sweet crepes, there’s a little something for everyone. Open daily until 9 p.m., they also scoop gelato from Il Laboratorio del Gelato. (Pro tip: They also have a selection of frozen dumplings ready for pick-up.)
New this summer, Blue Han is a Korean kitchen and cafe offering a menu of classics like tteokbokki and seafood and green onion pancakes. There are also signature trays with arrays of banchan, as well as larger dishes like bibimbap and various kimbap varieties. Sure to become a favorite on the island, it offers something different amongst the coastal European fares.
Don’t be intimidated! Preorder and pick up a bag of ready-to-shuck East End oysters from the no-frills Peeko’s stand.
This on-island cheese wagon is a delight of specialty cheeses from around the globe. With breads and spreads to help you complete the perfect cheeseboard, King Andrew Cheese will give you sample after sample to ensure you’ve found the perfect wedge for any occasion. Hours vary, but they have a stocked self-service fridge so you can get cheese even when the barrel-shaped cart is closed.
What to Do
At over 2,000 acres, Mashomack is a pristine and special nature preserve located right on the island. With walking trails ranging from half-mile loops to longer options with sweeping water views, expect exceptional bird and wildlife watching, including the occasional fox.
A charming, historic working farm on the island, Sylvester Manor has a small store with homegrown produce, various baked goods, and provisions from around the North Fork. Surrounded by fields of vegetables and flowers, take advantage of the walking trails across their 200-plus acres, which feature a seasonal sculpture show set amongst nature.
Inside the island’s only grocery store, a humble (but well-stocked) IGA is SPRMRKT, an island-themed streetwear shop inspired by the supermarket in which it’s sold. Founded by Anthony Peronace, whose parents own the market and who grew up stocking the shelves, their products play on the Shelter Island location and old-school supermarket iconography, making for unique, one-of-a-kind souvenirs. All products are designed and made on Shelter Island, and some are even packaged to look like butcher-counter meat, complete with styrofoam and plastic wrap.
You can hardly call any part of Shelter Island “downtown,” but Shelter Island Heights is the closest you’ll get. For a collection of shops within walking distance, there are various coastal-themed homewares and fashion accessories, including women’s clothing boutiques Purethread and Pure Soul Boutique. Just up the street, the small but curated Finley’s Fiction is great for new releases (in case you forgot your book for the beach).
A mecca of used books for 30 years, if you’re willing to do a little bit of hunting, you can find plenty of collectible titles and treasures.
