Its cachet is in direct proportion to the Hamptons' reputation for overcrowded, overpriced summer-share madness. This means that 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.
Details Sunset Beach, 631-749-1843 (rooms start at $175; open from May 18 to the end of September); The Chequit Inn, 631-749-0018 (rooms in summer start at $72; in winter, $65); The Dory, 631-749-8871; Shelter Island Kayak Tours, 631-749-1990; Ram's Head Inn, 631-749-0811.