For New Yorkers, a trip to Long Island is an escape to the sand – specifically Jones Beach (6.5 miles long, parking for, gasp, more than 20,000 cars) and Robert Moses State Park (5 miles long, 8,000 cars). But another 100 or so beaches line Long Island, some of them with remote outer beaches (Cedar Point in The Hamptons among them) favored by the surf-fishing/4-WD set. Not surprisingly, the Hamptons are blessed with the finest beaches, although exclusivity sometimes carries a hefty price tag: seasonal beach permits can range from $200 to $500. One way to beat the crowds? Bike to Wainscott Beach. The neighboring real estate is pricey, the parking facilities minimal, and the beach is priceless.
For a taste of the island, head for the North Fork. Some 20 wineries and vineyards thrive here, most offering daily tastings. (Paumanok, a family-owned vineyard founded in 1983, has won raves for its cabernet sauvignons.) For pit stops along the way, keep your eyes open for roadside farmstands where you’ll find strawberries in early summer, and apples and pumpkins in fall. Tack on a warp-speed tour of Long Island art by visiting the Parrish Art Museum in Southampton (paintings by William Merritt Chase and Fairfield Porter are always easy on the eyes), then relive the movie Pollock) by touring the home and studio of modern art giant Jackson Pollock, and his wife, Lee Krasner, in East Hampton.