Explore thousands of activities with free cancellation and no added fees.
Design your experience with airport transfers, excursions, day tours & more.
Get an insider's look in what to book before you travel.
The further you get from New York City, the better Long Island gets. The beaches, the historical mansions, the vineyards and the views become more and more compelling on the pretty eastern stretches along the 118 miles of this island. From exclusive resorts in the Hamptons to white sands on the South Shore, Long Island is a world away from the Big Apple and there are dozens of ways to enjoy the scenery, relax and chill out with a glass of locally-produced wine. Whether you’re a history buff or an outdoors type, you’ll find lots to enjoy on Long Island.
South Shore — New Yorkers lust after the beaches of South Shore and it’s easy to see why – the white sand dunes are a perfect contrast to the rolling waves of the Atlantic ocean. Jones Beach Island and Fire Island National Seashore are long narrow islands with the best beaches – Fire Island is quiet and car-free, full of forests, campgrounds and endless beaches.
North Shore — The Great Gatsby made famous the inner workings of the affluent private estates of the richest New York families on the “Gold Coast”. Although many of the mansions were torn down after the Great Depression, many more remain and you can poke around them, and play the guessing game as to which inspired F Scott Fitzgerald’s novel. Beaches here are less crowded, but no less beautiful.
The Hamptons and Montauk — The South Fork of Long Island is world famous as the place where the rich and famous hang out, and designer shops here are as likely as not to have the real designer behind the counter. The restaurants are among the best in the USA, and the beaches are peerless. Climb the Montauk Lighthouse and visit Sag Harbor museum to find out about the whalers who lived here before the celebrities.
North Fork — The vineyards that crisscross the countryside are the main event in North Fork. With 30 wineries to visit, you won’t be short of places to sample the local vintners’ craft. With a fantastic aquarium, museums and a water park, North Fork is packed with things to do.
The glorious beaches of Jones Beach and Fire Island are unmissable – the peacefulness has inspired generations of visitors. Jones is busier but there’s a beach for everyone, and you can rent bikes, go sailing and hike among the wild deer – or find a nightclub on the beach and party until the sun comes up. For history and culture, visit Southampton Historical Museum, Teddy Roosevelt’s summer home at Sagamore Hill, the Whaling Museum or Montauk Point Lighthouse. And if you’d like to find out about the people who lived here before the Vanderbilts, visit the Shinnecock Nation museum.
With hundreds of miles of beaches, there’s no shortage of water sports on offer. There are dozens of surf beaches, and you can hire kayaks at the tip of North Fork, or go scuba diving in “Shipwreck Alley”. Further out, you can go deep sea fishing or whale-watching or go on a relaxing paddlewheel cruise. Hike along the sea shore, and maybe follow the Washington Spy Trail to see where George Washington’s spies gathered intelligence during the War of Independence. In addition to the bountiful numbers of vineyards, there are plenty of farms to visit and of course some of the best restaurants in the world, as well as bars where you can find out exactly what they put in a Long Island Iced Tea.