Beginning in New York Harbor and sprawling east for 118 miles (190 km), Long Island is both the longest and the largest island in the contiguous United States. Outside the boroughs of Brooklyn and Queens, the island is home to 2 counties, 13 towns, and a slew of hamlets and villages. The island’s most iconic destinations are sprinkled along the Atlantic coast and include Long Beach, Montauk, and most famously, the Hamptons. On the east end of the island, North Fork is bursting with wineries and scenic coastal bluffs, while South Fork is known for its luxury mansions, upscale boutiques, and white-sand beaches. Whether you’re staying on Long Island or want to take a day trip from Manhattan, there are plenty of things to do and see in this laid-back escape.
Long Island has more villages and hamlets than celebrities who flock here in the summer. Even for those who call the island home, things can get a little confusing. To make it easy, these are the top vacation spots you need to know.
The southern end of Long Island really begins with Long Beach, a coastal barrier island just off the South Shore to the east of Queens. Easily accessible from Manhattan via the Long Island Railroad, the destination features 2 public beaches, bike rentals, and walkable neighborhoods with whimsical stucco-and-brick homes.
East of Long Beach is Jones Beach Island, another barrier island boasting a 6.5-mile (10.5 km) beach known best for its swimming. The west end of the park is home to an undeveloped area with native plants and migratory birds, while an outdoor amphitheater on the bank of Zachs Bay provides a spectacular venue for summer concerts.
Yet another of the barrier islands is Fire Island, an unspoiled wilderness with 31 miles (50 km) of pristine beach. This “island of no cars” is primarily accessed via ferry, and is easily walkable thanks to it being less than a quarter-mile (.4 km) wide. The island has been a vacation staple for the LGBTQ community since the 1960s, hosting many of the most over-the-top summer parties.
On the northeast end of the island is wine country, an enchanting destination where more than 60 vineyards flourish and over 30 wineries serve pours of their award-winning product. Here, in North Fork you’ll find charming inns, idyllic farmstands, and organic eateries.
Famous as a summer getaway for celebrities, socialites, and Manhattan’s elite, this string of South Fork villages is replete with grandiose homes, designer boutiques, trendy restaurants, and immaculate beaches. With the Parrish Art Museum, Bridgehampton Historical Society, and several performance halls, it’s also an ideal place to take in some culture.
Nestled in Gardiners Bay between the North and South forks, 27-square-mile (70-sq-km) Shelter Island is a haven of natural beauty. Grab a ferry from Greenpoint or Sag Harbor for a day of hiking, biking, bird-watching, or some of the most stunning kayaking in the region.
Located on the easternmost tip of Long Island, Montauk—locally nicknamed “The End”—is a picturesque hamlet known for its seaside lobster shacks, lush state parks, historic lighthouse, and world-class surfing. Though the area is only home to roughly 3,000 permanent residents, the population skyrockets in the summer with New Yorkers fleeing the city. Like the Hamptons, Montauk offers plenty of high-end resorts, but its selection of humble beach motels imbues the hamlet with a more casual vibe.
Gaze out upon the sparkling expanse of the Atlantic from the Montauk Point Lighthouse, the oldest lighthouse in all of New York State. For a small fee, you can climb the 137 steps to the top of the historic tower. Marvel at 360-degree views that seem to never end, and then head down to the museum to uncover fascinating exhibits on history, wildlife, and the local environment.
On the northwestern shore of the island, Sand’s Point Preserve offers equally stunning views of Long Island Sound, as well as the breathtaking architecture of early-20th-century castles. Wander the 300 acres (121 ha) of majestic gardens for a trip back in time to the most extravagant period of the “Gold Coast.” Scattered across the North Shore are more than a half-dozen other historic mansions converted to public use which offer visitors the chance journey back to a world of opulence that reached its peak in the 1920s. Pay a visit to magical estates such as the Vanderbilt Museum and Oheka Castle, the latter of which is said to have inspired the mansion in The Great Gatsby.
Renowned for their white sand, epic waves, miles of boardwalk, and spectacular sunsets, the beaches of Long Island offer everything you could want in the warm-weather months. In the spring and summer, there are countless places to swim, surf, kayak, and sunbathe. Jones Beach is an ideal spot for swimmers, while Ditch Plains in Montauk is known for its surfing thanks to it sensational and consistent waves. Sun-worshippers will want to flock to Main Beach in East Hampton and Southampton’s Coopers Beach—2 spots consistently named among America’s best beaches.
From the locations of key Revolutionary War dramas to the airfield where Charles Lindbergh began his famous flight to Paris, the history of Long Island comes alive at many museums, homes, and preservation sites. Travel the Long Island Heritage Trail once used by colonial spies, visit the former home of Theodore Roosevelt at Sagamore Hill, and dive into the history of flight at the Cradle of Aviation Museum.
Wine lovers rejoice on the North Fork of the island, named one of the Top 10 Wine Regions in the World by Wine Enthusiast magazine. With more than 60 vineyards and 30 wineries, there are any number of places to sip the latest award-winning vintage. Leave the worries of driving behind on a tour that takes you to 3 of the area’s best producers.
As a favorite destination of the rich and famous, it’s no surprise that Long Island boasts a plethora of chic shopping options to meet the elite’s need for retail therapy. Keep your eyes peeled for celeb sightings as you stroll the streets of the Hamptons, passing by shops like Club Monaco, Jenni Kayne, Zimmerman, and Cabana. Bargain-hunters will appreciate a visit to Tanger Outlets, where designer goods can be found for a fraction of the price.
Uncover hidden treasures and unexpected surprises at the museums and galleries spread across Long Island. At big sites like the Heckscher and Parrish museums, find work by acclaimed artists including Rodin, Pollock, and O’Keeffe. At the smaller galleries sprinkled throughout the hamlets, you can peruse work from the vibrant community right here on the island. If performance art is more your speed, there’s a passionate theater scene that reflects the latest movements of Broadway.
With its water park, museums, beaches, and aquarium, Long Island is truly a child’s playground. Let their imaginations ride wild at the interactive Children’s Museum, dive into an underwater world at the Long Island Aquarium, or cool off from the heat with the rides and attractions at sprawling Splish Splash Water Park.