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So the Hamptons might be glammed-up farmland, but it’s precisely this combination of city and country living—of the chic and the rustic—that makes this summer colony so alluring.

Cheat Sheet

  • Stay…at the chic Topping Rose House or contact Indagare to rent a home
  • Experience…the best of summer on any Atlantic beach at dusk
  • Splurge…at Southampton’s edgy-chic Tenet
  • Eat…at foodie favorite Highway or savor Italian cuisine at Dopo La Spiaggia
  • Drink…at Wölffer Estate Vineyard, the Hamptons’ best winery
  • Savor…the beautiful garden of artist Robert Dash at Madoo
  • See…the Herzog & de Meuron–designed Parrish Art Museum
  • Shop…for gourmet treats at Round Swamp Farm and Levain Bakery
  • Know…that that as an Indagare member you can contact our Bookings Team for assistance with customized recommendations and itineraries

Lay of the Land

On a map, Long Island resembles a fish, with its easternmost part divided into two forks (or fins) by the waters of the Peconic Bay. The Hamptons occupies the lower tip or the “South Fork” of this fish and is bordered by the Peconic Bay on the north and the Atlantic Ocean on the south.

A common misconception among daytrippers is that the Hamptons is relatively compact. In fact, the South Fork of Long Island encompasses a number of towns, all connected by one, long winding road (Route 27, which merges with the Montauk Highway).

Though a few purists maintain the Hamptons begins just east of the Shinnecock Canal (starting with the village of Southampton), the general consensus is that it starts further west, with the pinier, more laid-back towns of Westhampton Beach, Quogue and East Quogue. Here there are still outrageously expensive homes by the ocean (on Dune Road) and pristine side streets lined with Victorian mansions, but the boutiques and the overall feel is decidedly lower key.

Moving eastward, you’ll hit the towns of Southampton, Water Mill, Bridgehampton (Sagaponack), Wainscott, East Hampton, Amagansett and Montauk. Each has its own distinct vibe and personality. Southampton and East Hampton (the largest and glitziest of them all) have some of the prettiest town areas. These two towns are also where the highest number of fine restaurants, luxury boutiques and multi-million dollar estates are, putting the “tony” in Hamptony.

Sag Harbor, a former whaling village, lies on the inside of the fork, facing the Great Peconic Bay. Bridgehampton, site of the annual Hampton Classic Horse Show and Mercedes Benz Polo Challenge, is known for its horse farms and antique and furniture stores while Montauk, the South Fork’s easternmost point, is now such a hot spot in the summer that you can barely believe not too long ago it was a laid-back surfing community, full of quirky mom-and-pop shops and 1960s motels.

When to Go

The official Hamptons season begins on Memorial Day weekend and ends after Labor Day. Some return for the Hamptons International Film Festival, but come October the crowds—and the traffic—have pretty much cleared. As many Hamptons homeowners attest, fall and winter can be extremely beautiful—you get the beach and the streets to yourself and all those impossible-to-book restaurants no longer require reservations. Others maintain that the glitzy, glamorous crowds are what the Hamptons is all about. If you do decide to go in the off-season, note that some places shutter either for the entire winter or on weekdays, so calling ahead is imperative.

Getting There

Planes, trains and automobiles are the primary means of transport. Private planes fly into East Hampton; the closest commercial airport is MacArthur in Islip, which has flights from Palm Beach, Baltimore and other cities served by regional carriers. Sea planes and helicopters are the quickest way to go from city center to beach side, but pilots are finding their landing options narrowing as homeowners around Mecox and Shinnecock bays have voiced opposition in recent years. The Long Island Rail Road may not be glamorous but the express trains make it from Queens to Southampton in two hours, no matter how bad the traffic jams are. For those who don’t want to drive themselves the Hampton Jitney (www.hamptonjitney.com) or the Hampton Luxury Liner (www.hamptonluxuryliner) have regular coaches to and from the various towns into Manhattan from as early as 6 a.m. to 9 p.m., all year long. And of course, the vast majority of regular visitors brave the Long Island Expressway for the 80- to 100-some mile drive, which can take between two and four hours, depending on the traffic and how far east one travels.

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