Many people think Long Island is just the suburbs of New York City, but it’s actually a fascinating destination on its own, offering a variety of experiences for every traveler. And with so many of Long Island’s sites easily accessible, this is a destination not to be missed. Glamorous history, spectacular food and drinks, luxurious accommodations, phenomenal scenic landscapes—Long Island has it all. Here are our picks for Long Island’s must-see attractions, from Gold Coast mansions to vineyards in the North Fork.
For a peek inside the glitzy and extravagant world that inspired F. Scott Fitzgerald’s masterpiece, The Great Gatsby, make your way to the Gold Coast of Long Island, the easternmost section of the North Shore. Sands Point Preserve is home to three luxurious mansions: Castle Gould, Hempstead House, and Falaise. Built by railroad magnate Jay Gould’s son before being sold to the Guggenheim family in 1917, the estate is now a nonprofit preserve open to the public year-round. Take advantage of all the grounds have to offer: hiking trails, a barn and stables, an outdoor classroom, a rose garden, and access to a mile-long beach. It also hosts family programs, making this an experience the kids can enjoy too.
If your Gold Coast tour has you yearning for Gatsby-style mansion luxury, OHEKA Castle will fit the bill. Currently a full-service hotel, OHEKA was once owned by financier Otto Hermann Kahn and has had a tumultuous history. It served as a New York sanitation workers’ retreat and a military academy before being abandoned and falling into disrepair. Purchased by Gary Melius in 1984, the mansion is still being painstakingly restored to its former glory as it hosts weddings and other private events. However, you don’t have to be a guest to get a taste of this grand estate. The hotel has a bar and restaurant offering exceptional cuisine and cocktails. Tours of the mansion and grounds are open to the public as well.
Established over a century ago in Port Washington, Louie’s Oyster Bar and Grille is a Long Island institution. The dining room, decorated in rich wood and exposed brick, elevates the feel of this unpretentious spot, but it’s the outdoor deck that is the star, with panoramic views of the New York City skyline. You can’t go wrong with classic seafood fare like the creamy New England clam chowder or the namesake fresh oysters, but creative daily specials like the spicy lobster tacos give the menu contemporary and eclectic options. The key lime pie, an original recipe from 1905, and the decadent “Holey Moley” hot fudge sundae will make you glad you saved room for dessert.
Ardent history buffs will love Sagamore Hill National Historic Site, home to President Theodore Roosevelt for thirty-four years until his death in 1919. The grounds include a museum focusing on Roosevelt’s life, a visitor’s center, apple orchards, and the Sagamore Hill House itself. Only structural and restorative renovations were made; the layout and decor are still the same as when the twenty-sixth president walked the halls, animal heads and all. Guided tours will be intimate, up to fifteen people at a time, and will start every half hour. With the knowledgeable and passionate park rangers at the tours’ helm, this is the best way to get an insider’s glance into the life of Teddy Roosevelt.
With more than 50 wineries operating in the North Fork, wine lovers can’t miss this charming and low-key wine region. Start your tasting tour at Bedell Cellars, a family-owned winery established in 1980 that prides itself on its sustainable farming techniques. Taste a flight of five wines in its tasting room, elegantly styled in modern decor and contemporary art, or head outside to the picnic tables and enjoy a glass near the beautiful vineyards.
Next up, head to Shinn Estate Vineyards. Husband-and-wife team Barbara Shinn and David Page run this vineyard and bed and breakfast, adhering to biodynamic principles. The result yields wines with great complexity. Sip a glass of these acclaimed wines while relaxing in the rustic tasting room and outdoor space.
Martha Clara Vineyards, named for the matriarch of Entenmann’s bakery fame, is next. Wine tasting isn’t the only activity available at this family-friendly spot; the vineyard regularly hosts public events, live music, farm animals, and even horse carriage rides around the estate.
At the easternmost point of Long Island lies Montauk Point Lighthouse. Commissioned by President George Washington in 1792 and built in 1796, this quaint lighthouse is the oldest in New York and the fourth oldest active lighthouse in the country. Inside the keeper’s house you’ll find the museum, filled with artifacts, photos, and videos from this storied site, now designated a National Historic Landmark. Catch a tour or explore the museum on your own. If you’re not afraid of heights, climb the 137 steps all the way to the top for stunning views of Montauk Point State Park’s grounds and beaches.
Beachside dining in a laidback atmosphere is what you’ll find at Navy Beach. Tucked away from the main streets and overlooking Fort Pond Bay, this bar and restaurant focuses on fresh, local seafood. The beach- and seafaring-themed décor adds a whimsical feel, while the outdoor dining area provides a picturesque backdrop in a private setting. The menu is relatively consistent between lunch and dinner, which gives you a great opportunity to try dishes like the grilled sea scallops with arugula, snow peas, pea shoots, and chorizo brown butter or the truffled mac and cheese. After your meal, enjoy dessert or a refreshing cocktail on the back patio and get a glimpse of the wondrous sunsets this intimate bay has to offer.
If you’re looking for resort-style accommodations with a boutique-hotel feel, then Montauk Yacht Club Resort & Marina is the place to go. With 102 nautical-themed guest rooms built on 32 acres of land, there are enough activities (private beaches, surfing, sailing, pools, a spa, and nightly bonfires, just to name a few) on site so you never have to leave the property. The bar and two dining options, one for casual daytime meals and the other for a more formal dinner option, ensure Montauk Yacht Club has everything covered for a satisfying stay. If you do feel like venturing out, the charming town of Montauk is a short ride away thanks to the complimentary shuttle on premises.
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Also published on Medium.