Fire Island is a prime destination to celebrate resilience and rebirth. In 1938, a hurricane flattened the long, skinny barrier island (it’s 32 miles long but only half a mile wide). Some 9,000 homes were destroyed by high winds and 18-foot-tall waves. But what rose from the ruins is one of the most unique vacation ecosystems imaginable.
The largely car-free island is knit together by wooden boardwalks that serve as both streets and bike paths. Because most transportation is by foot, bike, or boat (water taxis and ferries), each hamlet has a unique character, and hopping between them—mixed with time lounging on Fire Island’s sweeping white sand beaches, of course—is an appealing way to while away a day (or four).
You might head to charming Kismet, which has a number of little shops, eateries, and a historic lighthouse, then to The Pines and Cherry Grove, LGBTQ+ havens known for afternoon tea dances and evening ragers. At Ocean Beach, the drink of choice is Rocket Fuel, kind of like a piña colada but with triple the liquor. The Sunken Forest encompasses a rare assemblage of trees protected by sand dunes and the National Park Service.
Be sure to study the ferry map carefully before you head out. Three different Long Island towns are connected to different ports on Fire Island, and it’s easy to hop on the wrong ferry.
Getting there: How you go will really depend on which Fire Island town you’re visiting. But one of the speediest ways to reach the island is to take the North Fork Express bus to Ronkonkoma, and then hop the ferry to Cherry Grove. Kismet is accessible by car, so many visitors take a train from Manhattan’s Pennsylvania Station to Babylon (1 hour, 15 minutes) and then hop a 15-minute taxi to the town.