Montauk technically sits within the boundaries of East Hampton, on Long Island’s South Fork. Unlike the tony Hamptons, though, which have long been an elite playground, Montauk has maintained an independent spirit that has given it a unique appeal. Fishermen, surfers, and some of New York City’s best artists have made it their home, and these days the destination is both supremely stylish and utterly relaxed.

Montauk is known for its outstanding angling, especially for big fish such as tuna, shark, and striped bass. By some accounts, the town holds more saltwater fishing records than any other port in the world. Montauk Yacht Club Resort & Marina keeps a fleet of charter fishing boats for guests’ use, maintains a custom-built, on-site fish-cleaning station and hosts a variety of tournaments throughout the year. The town is also an East Coast surf mecca, and surfing lessons or surfboard rentals can be arranged through the marina office or the resort concierge.