Embodying a “just right” balance worthy of Goldilocks, this 8,000-acre island caught like a pearl between the pincers of Long Island’s North and South Forks has sophisticated style and old-fashioned island authenticity in equal measure. Being accessible only by ferry infuses life here with a remote sensibility, despite being so close to wine country to the north, the buzzy Hamptons to the south, and the thrumming canyons of Manhattan just 90 miles west. But you’d never know it on a quiet morning: With just more than 17 miles of shoreline and four little harbors bobbing with boats of every size and purpose, Shelter Island is just that: a maritime gem hidden in plain sight—quiet, colorful, and staunchly original.
Shelter Island by the Numbers
- Classic East Hampton Summer House Tour
- Insider Guide to the Hamptons
- Double Take: Malibu vs. Montauk
Average July high: 80
Average January low: 24
Median home price: $888,700
Average commute time: 17 minutes
Number of sunny days: 206
Best Beaches and Other Attractions
Half-mile-long Crescent Beach has the island’s best sunsets, as well as a taste of the beautiful people who hang out here under the radar.
The Mashomack Preserve occupies the entire southeastern peninsula of Shelter Island, more than 2,000 acres of pristine oak woodlands, marshes, and creeks fringed with 12 miles of undeveloped coastline. Managed by the Nature Conservancy, the preserve has five hiking trails ranging from one to 10 miles in length, plus a water trail that explores the creeks and coast in Coelce Harbor.
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Where to Eat and Drink
An island favorite for visitors, locals, boaters, and the jet set, The Shipwreck Bar at SALT Waterfront Bar & Grill is 39-foot schooner that has been transformed into an open air bar serving drinks and food, and offering live music seven days a week in the summer months. Just don’t gawk at the celebrities that hang out here… the whole joy of Shelter Island is that it leaves the buzz of the Hamptons buzzing across the water.
One of Shelter Island’s loveliest 19th-century Victorian homes is now the address for the 18 Bay restaurant. Chef-owned, it has a seasonally changing menu based on local sourcing and availability: four-course, fixed-price dinners start with antipasto and lean toward Italian-inspired seafood dishes, finished with house-made desserts.
Where to Stay
Shelter Island got a cool-kid upgrade with the arrival of The Chequit, a sprawling Victorian built as part of a Methodist camp in 1872 and newly restored to charming perfection by David Bowd and Kevin O’Shea, who have added luxe touches (rain showerheads) while leaving the historic patina (worn floorboards) on the former camp dining hall, and the result is rustic fairy tale. Two other old-school buildings comprise the property, while a café along with the seriously cozy, local-catch-and-harvest-inspired Red Maple restaurant means you never have to leave the breezy compound. Why leave, when there’s complimentary Prosecco on offer, and a view from the wide porch of wooden sailboats bobbing in Dering Harbor?
A little off the beaten path even for Shelter Island, the 17-room Ram’s Head Inn has New England charm running from a spacious lawn seeded with Adirondack chairs for sea-gazing to sunset dining on a wide porch. The beachy farmhouse exterior of the Shelter Island House gives little hint of this inn’s brightly decorated second-floor suites: spa-inspired baths with jetted tubs and Cote Bastide toiletries encourage lounging in bathrobes, although you should eventually make your way downstairs to the lively tavern for cocktails, conversation, burgers and bourbon short ribs.