A small hamlet in the town of East Hampton, Amagansett offers all the charm of the Hamptons but has a somewhat more down-to earth character than its counterparts to the west, despite regular sightings of celebrity residents like Paul McCartney and Gwyneth Paltrow. The name comes from a Native American word meaning "place of good water," and in its early days the town's tranquil setting was perfectly suited to fishing and whaling. Downtown Main Street has retained many of its original buildings as private residences, shops, B&Bs, and good restaurants. There's also a small outlet center on the village green. The town’s Main Street is a designated historic district, so you will never find fast-food franchises here.
Need trip ideas? Get inspired by our curated collections of the world's best destinations.More