Long Island is a unique part of New York, home to approximately 8 million residents and stretching for 118 miles. It revolves around idyllic summers, but there's much to appreciate in its boho harbor towns and cute villages throughout the year, wherever your interests lie. You can dance the night away on Fire Island or sunbathe on white sand beaches. Artsy types can visit Jackson Pollock's house, to begin with, and foodies can try one of the many farm-to-table restaurants that dot the map. Long Island promises a stay as bougie or down-to-earth as your mood demands.
Mariah Carey is the Queen of Christmas, and her birthplace, Huntington in Suffolk County, is home to a chateau fit for royalty. Otto Hermann Kahn was a Jewish investment banker who wanted to build an estate with all the trappings of success at a time when Jews were denied entry to certain clubs. Oheka Castle was constructed two decades after the Gilded Age came to a close, but it's as opulent as anything built during that period. Kahn hired the sons of Frederick Law Olmsted of Central Park fame to design French gardens that wouldn't be out of place in Versailles. Oheka Castle is the second largest private residence in the U.S. and served as inspiration for Gatsby's house in The Great Gatsby. Its epic aesthetics have been featured in numerous movies, TV shows, and music videos like Taylor Swift's Blank Space. Famous folks like Kevin Jonas, Megyn Kelly, and Huma Abedin held their weddings here too.
This privileged East End enclave welcomed the fabulously wealthy way before Kourtney and Khloé Kardashian decided to 'take' it. Known for real estate with eye-watering price tags, the Hamptons is WASP central but also opens its arms to anyone who can afford it. You can shop at one of the many boutiques or seasonal pop-ups, attend polo matches, or try and spot celebrities. Check out the mansions with their manicured lawns, or head to Main Beach for the buzz. There's also the Big Duck landmark in Southampton—a 20-foot homage to the duck farms of old.
The 30-mile North Fork peninsula makes for a rewarding day trip and a satisfying longer vacay. The waterfront village Greenport is just a two-hour drive from Manhattan and is perfect for anyone keener on vineyards and farms than a beach. The culinary scene here is thriving, and you'll be able to indulge in more complex fare than a lobster roll, although these are also available along with super fresh oysters. Savor stunning sunsets while having a gourmet picnic, ride an antique carousel that generations have enjoyed over the last century, or ride a bike on the flat terrain. You might see lavender fields in bloom. Purchase organic produce on your way back home and drop in at the Horton Point Light.
Technically a part of the Hamptons, Montauk in East Hampton has a different vibe and used to be all about surfing and fishing. These days, it's become popular with a more sophisticated crowd, and you can gallery hop and dine in style. Visit the Montauk Point State Park to look for seals and climb the lighthouse for fantastic views. It's the fourth-oldest active lighthouse in the country, commissioned by George Washington. The lighthouse was also where the slave ship Amistad reached American soil. Here's a less depressing fact—conspiracy theories involving Montauk inspired Netflix's mega-hit Stranger Things.
Shelter Island lies between the North and South Forks and is accessible by car ferry from Greenport or North Haven. It comprises 8,000 acres and has around 1,600 full-time residents. Sunset Beach is glamorous, but as a whole, Shelter Island is much more of a laidback coastal destination than the Hamptons. You can pop in at art studios, collect shells at quiet Crab Creek, or attempt birdwatching and kayaking at the marshes in Mashomack Nature Preserve.
This mostly car-free stretch of South Shore is an LGBTQ haven, as depicted in the 2022 rom-com Fire Island. Highlights include the lighthouse built in 1858, which you can get to by car via Robert Moses State Park, and the Fire Island National Seashore. The latter has a party hub at Ocean Beach Village in addition to swimming beaches, hiking trails, residential hamlets, and camping opportunities.
Kids usually have a blast at The Jones Beach Nature Center, where they can dig for bones, see butterflies, and a shipwreck. The Memorial Day Bethpage Air Show is another event you'll want to jot in your calendar. The U.S. Navy Blue Angels draw oohs and aahs from the crowds with all their airborne feats over Jones Beach.
Long Beach isn't too far from Brooklyn and Queens, and it's worth the beach pass fee and hour-long train journey from Penn Station. The boardwalk is just over two miles long for your strolling pleasure and is dotted with cafes and fro-yo joints along the way. You can learn to paddleboard or show up in time for a free summer concert. The Long Island Railroad offers discounts on return trips, so keep an eye out for those.
Between the living history tours about the Gold Coast and its socialites and the natural history collections, you'll learn a lot at the former estate of William Vanderbilt II. Set aside at least three hours so you can soak up the gorgeous vistas, go on tours, and engage with the exhibits.
Horror and true crime enthusiasts might be interested to know that the notorious Amityville Horror House sits at 108 Ocean Avenue. It's a private residence, not a museum, but you can drive by for the goosebumps. Built in 1927, the house was the site of a tragedy in 1974 when 23-year-old Ronald J. DeFeo Jr. killed all six of his family members. His lawyers claimed voices told him to commit the murders. In 1976, the Lutz family bought the house but left shortly after moving in after supernatural phenomena supposedly drove them out. Since then, there have been four owners and no further incidents.