Fire Island, N.Y.
A mere hour outside of Manhattan, Fire Island is where we suspect the people who live year-round in the Hamptons might sneak off to for escape. The small community has been cultivating a bohemian, avant-garde vibe for decades. Fire Island loves to throw a party once the sun sinks into the sea, and the residents here pride themselves on open minds and easy-going attitudes. The mid-summer Invasion of the Pines Party is a legendary drag queen parade, which marches on land through the streets and continues on water with a packed ferryboat cruise. It’s a rare spot, nestled between the Atlantic Ocean and Great South Bay, which offers secluded, pristine sections of beach with a strictly enforced no-car policy on the island.
The sandbar surf breaks here are considered some of the best on the northeastern seaboard, and the island’s four sailing schools have cultivated generations of friendly rivalry, happily resulting in annual regattas. One life-long resident aptly described it: “If the Hampton’s idea of lunch is in a 4-star restaurant, complete with high heels and a tea-cup poodle, Fire Island’s take on lunch is a picnic on the beach, barefoot with a golden retriever.”
HINT: This island’s draw of small, beach cottage accommodations can also be a drawback. If you can, reserve early to ensure a spot, but last minute deals are also possible from cancellations. Watch Hill Marina & Camp Ground also offers the island’s only camping sites.