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The Top Long Island Spots

For Your Next Sweet Escape

by Our Editors
Bike Tricks for Two

Long Island boasts a vibrant LGBTQ+ scene, with a variety of hotspots catering to the gay community.

Escape to Long Island for an award-winning wine country, farm to table coastal cuisine, pristine beaches, historic villages, vibrant nightlife, and inviting LGBTQ communities.

Long Island, renowned for its storied past, breathtaking beaches, opulent estates, and exceptional dining options, has evolved into a premier global destination, drawing travelers not only from New York but from across the world. Here are five compelling hotspots showing why Long Island stands out as the ultimate summer getaway.

Fire Island

Fire Island, NY

Fire Island, NY

Known for its rich LGBTQ history, Fire Island is a beautiful barrier island that can be whatever visitors make of it. For parties, nightlife, and great socializing, Cherry Grove and the Pines are the places to be. Adorned with boutique hotels, vacation rentals, neighborhood bars and clubs, beachfront cafes, and more, the Pines and Cherry Grove are two local communities that pack a big punch. They epitomize “island life” and perfectly blend beach-side thrill and serenity.

Fire Island is car-free and has no paved roads, so to get there you must take a ferry or a water taxi, which is an experience in itself! Let the cool mist hit your face on the top floor of the ferry or stay on the first floor if you want some shade. Ferry terminals are in various locations, including Bay Shore, Sayville, and Patchogue.

Visitors will want to anchor their trips around the July 4th holiday. For the rest of the country, people are enjoying backyard barbecues for Independence Day… but out on Fire Island, the community is celebrating “the Invasion of the Pines.” Annually, a ferry full of drag queens arrives on the island. Adorned with pearls and feather boas, the queens usher in a day (and night) filled with celebration and excitement.

Sailors Haven is home to one of the best-known areas of Fire Island—the Sunken Forest. It is located near the center of the island, across the Great South Bay from Sayville, New York. In addition to the one-and-a-half-mile long boardwalk trail through the Sunken Forest, Sailors Haven also offers a visitor center, snack bar/convenience store/gift shop, picnic tables and grills, lifeguarded beach, and a public marina with electricity, water, restrooms, and showers. Perfectly equipped for a not-so-average beach day.

Lastly, Davis Park is a particular favorite if you’re looking for live music, soft sand, and a drink in your hand. It is home to one of the largest marinas on Fire Island, capable of holding up to 250 boats. It is accessible from the Davis Park Ferry terminal in Patchogue.

Wine Country

Bedell Cellars, Cutchogue, NY

Bedell Cellars, Cutchogue, NY

While Long Island is often seen primarily as a beach destination, through the stretch of over 118 miles there is a plethora of attractions beyond the sandy shores. Tucked in Long Island’s North Fork, the northern branch on the peninsula’s east end, is home to a flourishing wine country that’s made up of over 60 wineries and vineyards. The Long Island wine country is rated within the top ten wine regions in the world by the experts at
Wine Enthusiast magazine.

Immerse yourself in all things wine, from the grape to the glass by paying a visit to RGNY— a woman-owned winery that embraces the Mexican culture in which it was founded. RGNY even offers a horse-drawn tour around the vines, making a wine tasting experience there truly unique.

Consistently achieving 90+ point scores from Wine Enthusiast and additional worldly wine critics, Sparkling Pointe wines are recognized as among the finest in the region. Accompanying the delicious wine, one will find bright Brazilian artwork and influence throughout the Tasting House and the experience.

If your idea of a great vacation is savoring a crisp chardonnay or a robust merlot while the sun sets over a vineyard, the North Fork (or “NOFO” as the locals call it) is the perfect destination.

The Hamptons

Coopers Beach, Southampton, NY

Coopers Beach, Southampton, NY

Downtown Sag Harbor (Image courtesy of Discover Long Island) The Hamptons are one of Long Island’s most popular summer destinations and have been the home away from home for Manhattanites and A-list celebrities. This world famous region is made up of many enchanting coastal communities that serve as a haven for fashionistas, culture seekers, art enthusiasts, beach lovers and foodies alike.

For the art enthusiasts, Parrish Art Museum in Southampton is must-see. Showcasing the artistic legacy of Long Island’s east end since the 1890s, the museum has proven itself to be one of America’s most vital creative centers.

Hampton Bays holds the site of America’s oldest inn, Canoe Place. This east end landmark is a canal-front enclave featuring luxury accommodations, regionally inspired dining, and gorgeous garden views.

Once a whaling port, Sag Harbor is a small village with a charming downtown and Main Street that’s loaded with locally owned restaurants, antique shops, chic boutiques, and art galleries. Making the community even more special is that many of the historic homes and whaling cottages have been preserved and restored, giving Sag Harbor an old-school charm.

There are plenty of stunning beaches to choose from in the Hamptons, but a local favorite is Cooper’s Beach in Southampton.

Montauk

Montauk Lighthouse, Montauk, NY

Montauk Lighthouse, Montauk, NY

For those who want to truly escape to Long Island, a visit to Montauk is a must. Located at the very eastern edge of Long Island, Montauk is loaded with wildlands that are protected by a series of connected parks. Creating the massive preserve are Montauk Point State Park, Camp Hero State Park, Montauk County Park, and Amsterdam Beach State Park. From hiking to biking, camping, fishing, and even surfing, there are tons of activities to enjoy, all surrounded by stunning cliffs, crashing waves, and dense woodlands.

The most famous is the Montauk Point Lighthouse, which offers breathtaking views over the Atlantic, and has been preserved as a national landmark and museum. As the first to be built in New York State, it was commissioned by George Washington in 1792 and today remains the 4th-oldest operational lighthouse in the entire country.

In town you can expect boutiques, delicious seafood, and most restaurants flip-flop friendly. To truly relax in style, check into Gurney’s Montauk Resort & Spa on an oceanfront cabana.

Greenport

Off the coast of Greenport, NY

Off the coast of Greenport, NY

For something truly unexpected, discover the up-and-coming seaside community of Greenport. The town is becoming known for its trendy hotels and dining scene, like the American Beech Hotel, a stunning resort located in downtown Greenport. With modern, stylish rooms, popular bars, and restaurants with outdoor seating, you’ll feel more like you’re in Miami than on Long Island.

Greenport boasts its very first vineyard, the gorgeous Kontokosta winery. If you’d rather drink local beer for the day, take a visit to Greenport Harbor Brewing, which is located right in the heart of the village in a renovated 1860s firehouse.

Set sail with East End Charters for an unforgettable voyage along the shores of Long Island. The yachts provide the ultimate escape, where you can immerse yourself in the tranquil beauty of the coastline while experiencing personalized service and luxury
amenities.

For more info on Long Island visit their website or mobile app.


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