Long Island—the longest and largest island in the contiguous U.S.—is an adventure-filled playground, featuring world-class beaches, award-winning wineries, historical mansions, gorgeous gardens, and much more. And it’s all right in New York City’s beachfront backyard, an easy train ride away on the Long Island Rail Road. Here’s how to spend three unforgettable days there.
Hop the Long Island Rail Road or jump in a car: Your first stop is Long Island’s Gold Coast, home to lavish, early 20th-century estates and inspiration for the Great Gatsby. Begin your journey back to this era at the Vanderbilt Museum and Planetarium. This elegant Spanish Revival mansion, the former home of William Kissam Vanderbilt II (great-grandson of Commodore Cornelius), sits on 43 historic acres overlooking the Long Island Sound. Tour the mansion and museum galleries, then take in a fascinating show at the planetarium. Worked up an appetite? Tuck into the modern American menu at Prime, in Huntington Village, and dine with a view of the water. Then fully embrace the Roaring Twenties by spending the night at the sprawling, stunning Oheka Castle, which sits majestically atop Long Island’s highest point. Tour the mansion and gardens here, too, and see why it’s the backdrop for many Hollywood weddings and films, from the classic film Citizen Kane to the more recent TV series Royal Pains. Have dinner and cocktails at the elegant OHK Bar and Restaurant and stay overnight in one of the royal guest rooms.
Long Island boasts lots of impressive golf courses; start your morning by teeing off with spectacular views of the island’s southern shore at Timber Point Golf Course. Then head north to the quaint, nautical village of Port Jefferson and enjoy a seafood lunch with a water view at Danfords Hotel, Marina & Spa. Don’t linger too long, though; next up is the acclaimed vineyards of the North Fork, and you’ll want to leave plenty of time to explore. A wide range of grapes thrives out here; sample the delicious results at spots like Bedell Cellars, Sparkling Pointe Vineyard, and Kontokosta Winery. Pair local wines with dinner at the North Fork Table & Inn, where the unique seasonal menu features locally grown produce and fresh seafood. Then spend the night at the Sound View Greenport, set on a private beach overlooking the Long Island Sound; take in the view from your room’s waterfront deck.
Stocked up with North Fork wines, it’s time to explore the quaint towns and sandy beaches of the South Fork, home of the popular Hamptons region. Start by immersing yourself in Long Island’s artistic legacy at the Parrish Art Museum, perusing works from masters like Roy Lichtenstein, Jackson Pollock, and and Willem de Kooning. Get your luxury shopping fix in East Hampton’s boutique stores, then stop for lunch at The Lobster Roll in Amagansett, which has been serving fresh crustaceans for more than 50 years. Finally, head to the island’s eastern tip and climb the 137 steps of the iconic Montauk Point Lighthouse, authorized under President George Washington in 1792. After all that activity, Gurney’s Montauk Resort & Seawater Spa is the perfect place to unwind. Take a dip in the indoor seawater pool and enjoy panoramic ocean views, luxuriate in the Finnish rock sauna, then savor a fine Italian dinner with a view at the resort’s Scarpetta Beach restaurant before turning in. Wake early to watch the sunrise on Gurney’s private white-sand beach before heading home, reliving the magic of your Long Island experience.