Main Street is a picture-perfect vision of what an ideal town should be: leisurely, family friendly, featuring unique boutiques, and top restaurants. Add to that the cultural caché of the Bay Street Theatre with the celebrity caché American Hotel and you have a formula for the good life.

More Sag Harbor's pedigree as a major whaling port during the 1800s is evident in its architecture, which has been meticulously preserved by its house-proud owners of today. Walk down Sag Harbor's streets and you'll see grand Greek Revival mansions, old Victorians with all the gingerbread, charming cape cottages, and authentic saltboxes. Warm weather mariners have an embarrassingly rich array of marinas, yacht clubs, and docks to choose from. Sag Harbor's shores, with the vista of Shelter Island in the background, provide sand and pebble beaches with gentle waters. Those who hear the siren's call know that home is where their heart is: Sag Harbor. Less