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Shelter Island is nestled between the South and North Forks of Long Island. Crescent Beach, one of a handful of tranquil beaches there, is as Hamptons-esque as it gets, thanks to the glitzy Sunset Beach hotel nearby.
The bulk of Shelter Island’s 27 square miles are peacefully residential. Shaded streets are fit for neighborhood strolls, but consider renting a bike from Piccozzi’s Bike Shop ($25 per day; 177 N. Ferry Road, 631-749-0045, jwpiccozzi.com). Opt for a full-day rental and cycle east to Ram Island to spot historic manors perched on the pristine coast. Most beaches here are secluded and perfect for a private dip.
Among the main reasons for Shelter Island’s lasting tranquillity, is Mashomack Preserve, which encompasses nearly a third of the island and was made into a nature sanctuary more than 20 years ago to curb development. Only hiking is allowed (even jogging is forbidden) along the preserve’s marked trails. Walk past white coastlines, oak woodlands, freshwater marshes and tidal creeks, and keep a watchful eye out for the endangered ospreys populating the preserve.
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Shelter Island is only accessible via ferry. Ferry service is available on both the North Fork from Greenport and the South Fork near Sag Harbor, on a first-come, first-serve basis; if you’re driving from the city there tends to be less traffic on the way to Greenport. By train from NYC, take the Long Island Rail Road to Greenport, just steps from the ferry.
North Ferry: $11/one way vehicle and driver ($2 each additional passenger), $2/one way foot passenger (cash or check only); departures every 10 to 20 minutes
South Ferry: $14/one way vehicle and driver, $1/one way foot passenger (cash only); departures every 10 to 15 minutes
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Not much changes on Shelter Island. In fact, the only stir over the past year was the opening of one hotel, one coffee shop, one restaurant and one boutique — all of which are under one roof, The Chequit’s.
Known as the “un-Hamptons,” Shelter Island boasts zero traffic lights, just two liquor stores and under 3,000 residents. Unlike nearby East End destinations like Montauk, the island is unapologetically and consciously in a state of repose.
On Shelter Island, plan to relax. Here’s how.