From the tony South Fork to its rustic northerly counterpart, Long Island is both a playpen for the well-to-do and a calming, cozy respite.
ILLUSTRATIONS ESRA CAROLINE RĂ˜ISE

SIMON DOONAN
CREATIVE DIRECTOR, BARNEYS
“The best hangout is Sunset Beach on Shelter Island. We tend to avoid the bacchanalian evening scene. Lunch is fab and great for celeb spotting.”

OLIVIA CHANTECAILLE
CREATIVE DIRECTOR, CHANTECAILLE COSMETICS
“I love to do a beach picnic from Round Swamp Farm. They sell delicious local produce and prepared foods. My favorites are the chicken salad and the freshly baked pies.”

ROMAN ROTH
WINEMAKER, WOLFFER ESTATE VINEYARDS
“I enjoy playing golf at Montauk Downs, having lunch at the Beacon in Sag Harbor and watching Elvis movies at the Bay Street Theater.”
Image – Everett Collection
REMEMBERING A COUPLE OF CHARACTERS
In its glory days, Grey Gardens, a graceful 14-room estate in East Hampton, was home to the pedigreed Bouvier Beale clan (cousins of Jackie Kennedy). When Jackie’s aunt Edie Beale divorced in 1946, the mansion began its descent into disrepair. Together, bohemian “Big Edie” and her eccentric daughter “Little Edie” lived a secluded life among 52 cats and the remnants of their once-grand life. In 1975, the women became the subject of the Maysles brothers’ haunting documentary Grey Gardens (later a Broadway show). Today, the estate is owned by Ben Bradlee and Sally Quinn. Wrangling an invite can be tough, but if you want to drive past for a peek, ask a local nicely where it is.
Image – Courtesy of Vanderbilt Museum
THE NORTH SHORE’S GREAT ESTATES
Families of the Gilded Age chose to build their mammoth estates on Long Island’s North Shore. Several are now open to the public, giving a look into the curiously outsize lives of William K. Vanderbilt II, Teddy Roosevelt and the like. At Sagamore Hill, the Roosevelts’ retreat in Oyster Bay, walls are decked with buffalo heads and the great room is flanked by two tusks of an elephant once owned by the emperor of Abyssinia. At the Vanderbilt Museum in Centerport, there are shrunken heads from the South Pacific and jellyfish preserved in formaldehyde. Look out across the water from the veranda, and you’ll swear you see the light twinkling at the end of Jay Gatsby’s dock.
June 8th, 2010 at 12:08 am
Not to be petty, but I would hope that the writer of an article about a place as iconic as Long Island referencing a novel as iconic as The Great Gatsby would know the basic fact that the light was at the end of Daisy Buchanan’s dock. It was from his own house that Jay Gatsby would stare at the green light emanating from Daisy’s dock, a light that served to symbolize his romantic, and unachievable, dream of reuniting with Daisy.
August 10th, 2010 at 12:40 pm
How do you fly there through United? I can’t seem to find a United flight to ISLIP
August 10th, 2010 at 1:34 pm
Hi Paula. It’s an easy drive from New York’s JFK or LGA airport, both of which are serviced by United. Happy travels.