11 Reasons to Visit Long Island Now

Jennifer Arnow

Many people think Long Island is simply 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 via train or car, 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.

By Jennifer Arnow

Jennifer Arnow

Gold Coast Mansions

WHERE: Sands Point and Old Westbury, New York

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.

A stroll through the breathtaking scenery of the Old Westbury Gardens will have you daydreaming about the region’s fabled past. The English manor-style mansion built by John Shaffer Phipps in 1906 is still fully furnished with turn-of-the-century pieces and original artwork. The magnificent grounds contain 90 acres of tranquil beauty, consisting of walled gardens, a lake, fountains, a thatched-roof cottage, and numerous picturesque plants and flowers. Old Westbury Gardens also hosts classic car shows, concerts, and horticulture workshops.

PLAN YOUR TRIP: Fodor’s Long Island Travel Guide

Jennifer Arnow

OHEKA Castle

WHERE: Huntington, New York

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.

PLAN YOUR TRIP: Fodor’s Huntington Travel Guide

Jennifer Arnow

Louie’s Oyster Bar and Grill

WHERE: Port Washington, New York

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.

PLAN YOUR TRIP: Fodor’s Port Washington Travel Guide

Jennifer Arnow

Sagamore Hill National Historic Site

WHERE: Oyster Bay, New York

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. After closing for a three-year renovation, the house will open to the public July 12th. 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.

PLAN YOUR TRIP: Fodor’s Oyster Bay Travel Guide

Jennifer Arnow

North Fork Wine Tasting

WHERE: North Fork, New York

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.

PLAN YOUR TRIP: Fodor’s Long Island Travel Guide

Jennifer Arnow

Long Island Spirits

WHERE: Baiting Hollow, New York

If wine isn’t your thing, Long Island Spirits might be more your speed. This craft distillery, nestled right in the North Fork, opened in 2007 and is the first of its kind on the island since the 1800s. The turn-of-the-century renovated barn is where Long Island Spirits’ artisanal distillers make their small batch liquors, such as single malt whiskey, sorbetta liqueurs made from fresh fruit, and their famous LiV Vodka. The tasting room offers the option to try the liquors straight up in a flight or mixed into specialty-crafted cocktails. Head to the sunny outdoor deck for your tasting and scenic overviews of the distillery’s farm.  

PLAN YOUR TRIP: Fodor’s Long Island Travel Guide

Jennifer Arnow

Topping Rose House

WHERE: Bridgehampton, New York

For the ultimate in luxurious accommodations, a stay at Topping Rose House is a must. Once the home of judge Abraham Topping Rose, this fully restored mansion boasts twenty-two lavish guestrooms, a tranquil day spa, and a chic farm-to-table restaurant created by founded chef Tom Colicchio. The property also houses a one-acre farm that supplies the restaurant, a barn and event space that hosts yoga classes, and a swimming pool. Topping Rose House is centrally located to all the sites Bridgehampton has to offer, so grab one of the complimentary bikes and hit the town or take a scenic ride down to one of the nearby beaches.

PLAN YOUR TRIP: Fodor’s Bridgehampton Travel Guide

Jennifer Arnow

LongHouse Reserve

WHERE: East Hampton, New York

Founded by renowned textile designer Jack Lenor Larsen in 1991, LongHouse Reserve is a serene art sanctuary on 16 acres of manicured gardens in East Hampton. The sweeping landscape, developed by a team of designers under Larsen’s oversight, is meticulously occupied by sculptures from major artists like Kiki Smith, Sol LeWitt, and Willem de Kooning. The sculptural exhibits are updated annually, and the various flora change up the scenery depending on when you visit. For a more hands-on experience, LongHouse offers plant and flower workshops, events, and even meditation classes. The interplay between the soft, lush landscapes and stark, industrial sculptures will inspire all who take the time to explore this alluring site.

PLAN YOUR TRIP: Fodor’s East Hampton Travel Guide

Jennifer Arnow

Montauk Point Lighthouse

WHERE: Montauk, New York

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.

PLAN YOUR TRIP: Fodor’s Montauk Travel Guide

Jennifer Arnow

Navy Beach

WHERE: Montauk, New York

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.

PLAN YOUR TRIP: Fodor’s Montauk Travel Guide

Jennifer Arnow

Montauk Yacht Club Resort & Marina

WHERE: Montauk, New York

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.

PLAN YOUR TRIP: Fodor’s Montauk Travel Guide