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By Tracey Minkin
The heart of Sag Harbor beats most strongly on Main Street, where Long Wharf is a gathering spot known for the town's iconic windmill. Locals also love Long Beach's three miles of white-powder sands.
Where to stay: Check in to the 1846 American Hotel—still the social hub of town, with eight bedrooms and a 75-foot yacht for rent. Call for seasonal rates; theamericanhotel.com.