The Island

Nestled between the North and South forks of Long Island, Shelter Island is protected from coastal storms and accessible only by ferry.

From the moment you get on the ferry, you feel like you have entered a different world, more like a small town in northern New England than an island on the doorstep of the Hamptons and New York.

Within easy access to the wealth of cultural, dining, shopping, beaches and vineyards of the North Fork and the Hamptons, it remains untouched by the more frenetic pace one finds “off island.”

In fact many people refer to Shelter Island as the “Anti-Hamptons.” “Quiet, windswept and casual” and “calmer, cooler and less crowded” are descriptions that New York Magazine has used to describe the island.

Shelter Island has become pretty darn popular. Amazingly, however, it’s still pretty darn idyllic. You can enjoy its pleasures in one of two basic ways. Check into Andre Balazs’s Sunset Beach and hobnob with South Shore celebrities and Euro imports plucked from Positano. Or slum it at one of the local inns like the Chequit, in the Heights, and forgo shrimp summer rolls and salsa for a game of pool and a burger at The Dory restaurant.

Either way, this surprisingly hilly island sandwiched between Long Island’s North and South Forks is a perfect mix of low-key charm and four-star setting. The beach is not the silk sand of the Hamptons, but calmer Peconic Bay is better for sailing and windsurfing.

Get a guided two-hour kayak tour of the island, much of which is actually a nature preserve, or bike out to Little Ram Island to the east for a drink at the colonial Ram’s Head Inn, famous for its view.

Sarah Bernard, New York Magazine