The white sands of Westhampton Beach burn my bare feet as I come out from the shade cast by my cabana, which is tended by servers. I find relief in the Atlantic Ocean as salty waves roll in. My 14-year-old daredevil son, Max, pedals into the water aboard a buoyed bike, shrugging off my worries, saying he is surrounded by "a SWAT team of lifeguards." My other son, 12-year-old Caleb, reports that Ryan Seacrest called him "Champ" after he retrieved a pingpong ball for him and Eli Manning.
This is life at the Dune Deck, a cedar-shingled beach club 80 miles east of Manhattan, that opened for the rich and famous in 2017. We're guests of generous friends, but our time here has shown us how privileged the area known as the Hamptons can be, if you can afford a rental or the reported $365,000 beach club membership fee.
To be clear, the Hamptons isn't one place, but a collection of old towns, hamlets and villages on the southeastern peninsula — or the South Fork — of New York's Long Island. In the early 1600s, English Puritans settled the area and farmed, fished, whaled — and even once held a witchcraft trial. In the late 19th century, Long Island Rail Road service expanded. Wealthy New Yorkers, eager to escape the sweltering heat of the city, began seeking refuge on the South Fork's bright white beaches. The hedged-in oceanfront estates they built through the 20th century can go for up to nine figures today.
Despite nearly 50 miles of coastline, the Hamptons can be a difficult place to access a beach. Many require parking permits that you buy in advance, and they frequently sell out, especially in celebrity-laden East Hampton Village. In the past, we've schlepped kids across the hot pavement to Coopers Beach, a full-facility public beach in Southampton that's consistently ranked one of the best in the U.S., where a daily parking permit goes for $50.
Fortunately, the Hamptons is more than a party destination for celebrities and beach lovers. On this trip, Caleb and I set out from Westhampton on a road trip to uncover the area's historic origins.
Where to go?
Each town in the Hamptons has a different feel. In the past, we've gone to old-money Bridgehampton to attend its annual horse competition, the Hampton Classic (Aug. 25-Sept. 1). Art lovers flock to East Hampton to tour the modest 1879 home of Jackson Pollock and Lee Krasner, while wine connoisseurs indulge at Wölffer Estate Vineyard in Sagaponack.
For our road trip, Caleb voted we go to Montauk, a reawakened fishing village at the far eastern end where rough waves make for some of the best surfing in the U.S. Climbing the 110-foot Montauk Lighthouse that was built in 1796 to guide ships in was on my bucket list. But I was an inexperienced surfer, sure to get slammed into rocks. I appealed to his love of Moby Dick to get him to go to family-friendly Sag Harbor, an 18th-century whaling port, instead.
We exited Montauk Highway and wound through the idyllic countryside, passing windmills, vineyards and farm stands before reaching the showier homes. It left us feeling like there were two Hamptons, and we liked the low-key one better.