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Spending the summer in the Hamptons

by AndrewStone May 2014 - last edited September

Want to rub elbows with the New York elite? Then spend the summer in the Hamptons. Take a look at our guide to where to stay and what to eat and drink on your Hamptons holiday.

Houses along Bridgehampton Beach | Spending the summer in the Hamptons

Houses along Bridgehampton Beach © Keith Levitt Photography/iStock/Thinkstock

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.

Ocean front houses | Spending the summer in the Hamptons

Oceanfront houses © Amy Walters/iStock/Thinkstock

For decades, New Yorkers have headed to a collection of towns on the South Fork of Long Island—a quick drive out of the city (minus the traffic)—called the East End, otherwise known as the Hamptons. F. Scott Fitzgerald wrote of East Egg and West Egg in The Great Gatsby, and his decadent description of grand mansions, manicured lawns, and swirling society happenings is 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 vacation 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.

Sunset on the water | Spending the summer in the Hamptons

Sunset on the water at the Hamptons © Emily Dickinson/Flickr

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 Sea Grille. Meanwhile, the Capri Hotel in Southampton combines all the right elements for cosmopolites on holiday—sleek, upscale room amenities; a world-class restaurant (BLT Steak); a great location near the region’s top bars, shops, and eateries; and The Bathing Club, a beautiful pool and manicured sun-soaking oasis. And the new Topping Rose Housein Bridgehampton is a luxury hostelry, through and through, complete with a Naturopathica spa, heated pool, an on-site Tom Colicchio restaurant, house vehicles by Lexus, and beautifully appointed rooms.

Lighthouse at Montauk Point | Spending the summer in the Hamptons

Lighthouse at Montauk Point © Mishella/iStock/Thinkstock

There are countless worthy restaurants, nightspots, boutiques, and snacking spots 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 new American spot Nick & Toni’s; Three Mile Harbor-adjacent East Hampton Point, which serves fresh catches within the resort of the same name; refined and romantic Red Bar Brasserie in Southampton; and Bridgehampton’s Almond, which takes full advantage of fantastic locally-grown ingredients and has long been recognized as one of the very best eateries of the East End.

Header image: Montauk Point lookout binoculars © Velllena/iStock/Thinkstock

Virgin Atlantic operate direct flights to New York from London Heathrow. Book your flight today.

Have you spent the summer in the Hamptons? Where were your favourite Hamptons holiday spots? Let us know in the comments section below.

Written by Andrew Stone

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About the author: AndrewStone

Andrew Stone

A Brooklyn-based writer and editor, Andrew Stone covers architecture and design for Interior Design magazine and is the former editor-in-chief of Los Angeles Confidential. A busy bee within the worlds of culture, style, and dining, he has interviewed celebrities and hot shots aplenty for various publications. Stone nurtures his two-decade love affair with his city as the resident Manhattan reporter for Hg2.com. Stone is the author of both Hg2 New York and Hg2 Los Angeles. What makes him a hedonist? "The desire to have firsthand knowledge of life's great offerings."