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Fire Island, New York

“This might seem a surprising choice, but imagine a 32-mile long barrier island—and National Seashore—just 50 miles east of Manhattan. No cars, just bicycles and wagons and bare feet. Fire Island is the Hamptons without the attitude,” says Greenberg, who has lived there, at least part-time, since infanthood. Accessible via ferry, the island is home to 17 different resort communities, a massive white-tailed deer population, plus extraordinary stretches of sand dune–edged beaches. “It is a place I return to every year in April, May, June, and again in September (the most magical month), where I can relive my youth, my freedom and my innocence.”