Where to stay, dine, and play in Long Island’s coolest coastal town.
Montauk, at the easternmost point of Long Island, has been colonized by fashion-forward boutiques and hotels that are one-upping the rest of the Hamptons with a refreshingly relaxed sense of style.
Tips: Montauk is approximately 120 miles from New York City—upwards of three hours by car or the Hampton Jitney (hamptonjitney.com; one way from $30) bus. The trip takes three hours by Long Island Rail Road (mta.info; one way from $15). The most direct driving route is the Long Island Expressway, to exit 70 (Manorville), then Route 27 East all the way to the end.
Sunset Surf Shack
If you want to take surfing lessons, head to the Sunset Surf Shack and ask for owner Craig Lieder, a quintessential hang-ten dude.
Surfer chicks - and their moms - love Haven for its flirty frocks, Brazilian jewelry, and vintage finds (a Pucci longboard, Midcentury Modern vases).
Striped Breton sailor tops hang from driftwood displays at this fair-trade- and organic-focused shop. Its owner, Joelle Klein, used to be a designer for Calypso Christianne Celle.
Former models Marylynn Piotrowski and Staci Dover are the tastemakers behind this source for bright espadrilles, sailcloth totes, and other beachy finds.
With stores already in Manhattan and Tokyo, this vintage boutique recently opened a Montauk outpost.
Montauk Yacht Club
The 80-year old island staple, where Charles Lindbergh once visited, gave its 107 rooms a multimillion dollar overhaul in 2009. The property has a scaled-down replica of the town’s famous lighthouse, not to mention three pools, four tennis courts, a spa, and a marina.
Solé East Beach
The low-key property is a revamped oceanfront motel.
Solé East Resort
The low-key Tudor-style hotel has beachy accents like sisal carpets and wood-burning fireplaces.
Owned by a team of New York City club impresarios, the Surf Lodge made a splash when it opened its 32-waterfront rooms on Fort Pond in the summer of 2008. The property includes a tiny Tracy Feith shop filled with caftans, a restaurant helmed by Top Chef star Sam Talbot, surf movies on rotation 24/7 in the lobby, and an open-air deck that doubles as the Hamptons' hottest nightspot. The property had come under criticism for its crowds of late-night revelers: the new management promises a more mellow scene, so you can peacefully sip mojitos by the waterfront fire pit.