Navigating the Upper Crust of the East End

Montauk

Carl Fisher, the same developer single-handedly responsible for transforming an uninhabited Miami Beach into one of the most popular resort destinations in the world, also played a huge part in the development of Montauk. After establishing Miami Beach, Fisher went in search of a new challenge and found it on the tip of Long Island. He purchased 10,000 acres in 1925 and began developing what he hoped would become the Miami Beach of the north. (“Miami in the winter, Montauk in the summer” was his slogan.) He opened the Montauk Yacht Club in 1929, and the rest, as they say, is history.

The Montauk Yacht Club Resort & Marina (32 Star Island Road; 631.668.3100) underwent a multimillion-dollar redesign and renovation in 2009, which preserved its history while adding the modern comforts discerning travelers’ demand. While the property features fantastic hotel accommodations and villa cottages, a full-service spa, fitness center, private beach, three swimming pools, tennis courts, and more, the world-class marina, part of the Ft. Lauderdale-based Island Global Yachts’ portfolio, is the crown jewel of amenities. The 232-slip, full-service marina can accommodate megayachts up to 275 feet, one of the few marinas on the entire East Coast that can do so. Continuing the property’s South Florida ties, Gulf Coast Kitchen by Robbin Haas (who established himself as one of the top Miami chefs in the 1990s) opened for the 2010 season. It’s fitting, given Fisher’s original vision for the town.

Shelter Island

Nestled between the North and South Forks, this once-secluded island (accessible by ferry from either Fork) got infused with hotelier André Balazs’ unique form of hip with the opening of Sunset Beach (35 Shore Road; 631.749.2001). But traditionalists needn’t fret; this seasonal property embraces the island’s laidback mentality, which called to a scourge of international high-profile types who have been snatching up property on the island for years. The hotel only offers 20 guest suites (each with a private sundeck), but visitors are welcome at the beachside Restaurant + Bar, featuring French bites that are perfectly complemented by a glass of Balazs’ Reserve Rosé.