Situated between Long Island's celebrity-studded Bridgehampton and East Hampton, this whaling town turned artists' and writers' colony only two hours from New York City has maintained its cozy, small-town identity for decades. From the annual Memorial Day parade to the arrival of Santa on the fire truck as the Christmas tree is lit each December, life for the 2,169 people here remains blissfully fun.
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.