Jet Charter Flights To Amagansett, New York

Venture to sights like Napeague State Park and Atlantic Avenue Beach as you discover Amagansett—a seaside area also notable for its beaches.

Every year from Memorial Day through Labor Day, the Hamptons become a notoriously see-and-be-seen summer getaway for wealthy New Yorkers, celebrities and those who want to be in close proximity to the aforementioned groups. Yes, the beaches are beautiful and so are the homes, but traffic is bad, restaurant reservations are hard to come by and crowds are at their peak. Simply put, it can feel like a hectic Saturday night in Manhattan rather than a relaxed beach vacation.

That all changes in the off-season (September through May), when the Hamptons—Westhampton, Bridgehampton, Southampton, Sag Harbor, Amagansett, East Hampton, Water Mill and Montauk—empty out and it becomes possible to enjoy the unique charms of this collection of seaside communities. There are plenty of year-round activities to enjoy, the weather can be quite pleasant depending on the month and hotel rates drop dramatically. It may seem counterintuitive to visit a summer resort area when it’s not summer, but rest assured that, aside from the very dead of winter, the Hamptons are a worthwhile destination. Here are five of the best reasons to head to Long Island’s East End in the off-season.