The Hamptons is group of towns and hamlets that the dot the South Fork of Long Island. "The Hamptons" is also a socially loaded phrase that refers to old real estate, new money, traffic jams, pickup scenes, surfers, ands SUVs. (For further explanation, see A Field Guide to the Hamptons).
Most of the action happens in Southampton, Bridgehampton, East Hampton, Sag Harbor (from which you can access the Shelter Island ferry) and Montauk. Best times to go are summer and fall, when you can take advantage of the pristine Atlantic beaches, farmstand bounty, and wineries. Things quiet down in the off-season (check restaurants and shops for seasonal hours).
HOW TO GET THERE →
By car, Long Island Railroad, Hampton Jitney, or Hampton Luxury Liner. André Balazs offers 45-minute trips (NYC to East Hampton) aboard an eight-passenger Cessna (yes, it's that kind of town). You'll need wheels to get from one Hampton to another. Otherwise, a bicycle can often do the trick.