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.
Author Sarah Horne
DAY TWO | Stretch your limbs and begin packing your bag. Before checking out, ask for a voucher for breakfast across the street at The Golden Pear Cafe (1), where you’ll order a bagel and coffee and check your portfolio in the New York papers.
Back in the Jag, you turn up Hampton Road to Route 27 and head farther out on the South Fork, wending your way through the villages of Water Mill and Bridgehampton, where you follow in the footsteps of Truman Capote and Jackie Kennedy and stop for a caffeine top-up at the Bridgehampton Candy Kitchen (2). This is the Hamptons institution where CEOs connect with their inner fi ve-year-olds, indulging in burgers and fries followed by double cones packed with mint chocolate chip ice cream.
Arriving in East Hampton, you check into The Hedges Inn (3), a polished inn overlooking a pond where swans bask in the dappled light. Where Southampton looked quaint at first glance, East Hampton is less coy about its ritziness. On its Main Street, there are ample opportunities to shop for diamonds, swathe yourself in Hermès scarves or drop thousands on alligator-skin bags.
Yearning to see what the area was like before all the fuss, you head into Springs, the Hamptons’ more workaday, bohemian enclave north of Montauk Highway, and pull up at a simple farmhouse, the Pollock-Krasner House (4), where Jackson Pollack lived with his wife, Lee Krasner, from 1945 until he died in 1956. In the barn studio where he laid his canvases, trade your shoes for slippers and walk across the floorboards where his stray splatters have been lovingly preserved.
Next, drive south to Amagansett for lunch at La Fondita (5), a surprisingly authentic roadside spot. Order the Baja-style fish tacos and grab a table outside, feeling lazy in the noontime sun. Yes, that is Gwyneth Paltrow in her yoga clothes at the next table. Act like a local—pretend you don’t notice.
At the nearby Amagansett Beach & Bicycle Co. (6), you leave the Jag behind. Rent a bike for the afternoon and grab a map before setting off down the Old Stone Highway to check out Napeague Bay (7). Have a look at the refurbished fishing shacks on stilts at the end of Gerard Drive, then make your way back to the beach at Louse Point to watch the windsurfers skim across the bay.
Now on a quest for land’s end, you pedal east on Montauk Highway, coasting through miles of Russian olive trees and scrub pine and into Montauk’s Hither Hills State Park. It’s a challenge to bike the salty old hills of salty old Montauk, but when you spot the 1797 Montauk Point Lighthouse (8) ahead, it all seems worth the effort. At nearby Money Ponds, where Captain Kidd is said to have buried untold treasures, you scan the horizon for pirates.
Seeing none, you ride back at a leisurely pace, return your bike and head to the Hedges for a hot shower. Once you’ve recovered from your exertions, it’s on to Nick & Toni’s (9), an unassuming but luxe nightspot where Hollywood royals gather for well-executed Italian fare. Order the rich goat cheese risotto and the day’s catch served with vegetables from the North Fork’s Satur Farms. Air-kiss Steven Spielberg on your way out.