Want to rub shoulders with the New York elite? Then spend the summer in the Hamptons. To guide your upper-crust adventures, we’ve rounded up the best places to sleep, sip, and dine in style during your next Hamptons stay.

Ask any card-carrying New Yorker: The key to enduring happiness in the Big Apple is to get out of town, frequently and in the grandest style possible. In order to survive the gridlock and bustle, New Yorkers seek out pastoral landscapes, quaint town squares, bucolic docks, and grand gardens, with plenty of world-class restaurants and scintillating nightlife thrown in for good measure.

For decades, New Yorkers have headed to a collection of towns on the South Fork of Long Island — a relatively quick drive out of the city, if the traffic’s behaving — known as the Hamptons. F. Scott Fitzgerald set The Great Gatsby in this part of the world, and his decadent descriptions of grand mansions, manicured lawns, and swirling society happenings were all true and then some. Should you wish to summer in the Hamptons yourself — for a weekend or an entire season — here are some resources to consider.

A variety of websites can connect you with a well appointed home in one of the Hamptons’ various hamlets. Hamptons Rentals is a logical place to start, with its strong selection of year-round and short-term rentals throughout the East End. Home Away is an indispensible resource for those in need of a holiday home rental, featuring top-tier listings posted by homeowners or property managers. Big-name realty companies like Corcoran and Douglas Elliman have rental divisions, which list some exclusive and fantastic listings, updated daily. Flipkey is an easy-to-navigate site that takes the guesswork out of selecting a size- and amenities-appropriate home away from home. And then there’s Airbnb, the online sensation that lets homeowners offer their unique, personal slices of life to visitors who crave a homey environment.

Should you prefer to go the hotel route, we first and foremost recommend The American Hotel in Sag Harbor — as lovely and classically all-American as can be in the centre of this former whaling village. Gurney’s Inn Resort & Spa in Montauk imbues your stay away with luxurious spa treatments, dramatic views, and fresh seafood at the on-site Scarpetta Beach, a sister restaurant to Manhattan’s much celebrated Scarpetta. Meanwhile, the Capri Hotel in Southampton combines all the right elements for cosmopolites on holiday with sleek, upscale room amenities and a great location near the region’s top bars, shops, and eateries (not to mention The Bathing Club, a beautiful pool and manicured sun-soaking oasis). The Topping Rose House in Bridgehampton is a luxury hostelry, complete with a spa, heated pool, an on-site restaurant, house vehicles by Lexus, and beautifully appointed rooms.

There are countless worthy restaurants, nightspots, boutiques, and snacking destinations throughout East Hampton (Sag Harbor, Wainscott, East Hampton village, Springs, Amagansett, and Montauk) and Southampton (Southampton village, Sagaponack, Water Mill, Bridgehampton, Westhampton Beach, Westhampton, Quogue, East Quogue, Amagansett, Bridgehampton, and Montauk). Some of our enduring favourites include: East Hampton’s timeless American spot Nick & Toni’s; Three Mile Harbor-adjacent East Hampton Point, which serves fresh catches within the resort of the same name; Hoppy house-brewed beer at the Dancing Man Brewery in Southampton; and Bridgehampton’s Almond, which takes full advantage of fantastic locally grown ingredients and has long been recognised as one of the very best eateries of the East End.


Written by Andrew Stone

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