5 Reasons to Escape to Long Island this Summer

Long Island is an excellent travel destination thanks to its beaches, wineries, local hotels, history, and great shopping and dining and thriving LGBTQ communities.

With its rich history, gorgeous beaches, stunning mansions, and great dining experiences, Long Island has undergone a massive transformation in the last few decades, becoming a world-class travel destination that attracts visitors from not just New York, but from around the globe. Here are five reasons why Long Island is the perfect summer escape.

Fire Island

Invasion of the Pines (Photo: @icepalacefi)

Long seen as an LGBTQ vacation destination, 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 go. Adorned with small, local hotels, vacation rentals, neighborhood bars and clubs, beachfront cafes, and more, the Pines and Cherry Grove are two small communities that pack a big punch. They epitomize “island life” and perfectly blend excitement and relaxation.

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

Wine Country

Vineyard in the North Fork region (Photo: James Kirkikis)

For many people, Long Island is considered a beach destination, but in reality the “island” is actually massive, spanning over 118 miles long. In fact, Long Island is even larger than the state of Rhode Island and is almost as big as Delaware. This means the island has much more to offer than just beaches. In fact, Long Island’s North Fork, a giant branching peninsula on the island’s north side, is home to a flourishing wine country that’s made up of over 60 wineries and vineyards.

The region is loaded with vineyard tours, tasting rooms, fantastic restaurants, and quaint inns. In fact, some of the vineyards, like Rose Hill and Jamesport, even have lodging right on their property. If your idea of a great vacation is one loaded with fantastic food and drinks, North Fork’s wine region is the place to be.

Sag Harbor

Downtown Sag Harbor (Image courtesy of Discover Long Island)

These days, travelers are looking for more authentic travel experiences, and Sag Harbor is the perfect destination for doing just that. Once a whaling port, Sag Harbor is a small community with a charming downtown and Main Street that’s loaded with locally-owned restaurants, antique shops, 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 authentic and rustic charm. Activities in Sag Harbor include sailing lessons, lounging in the sand at Havens Beach, and visiting the Whaling and Historical Museum. The must-stay lodging option is the American Hotel, which was built back in 1846. With a great location directly on Main Street and a highly-regarded restaurant, it’s the perfect spot for first-time visitors.

Montauk

Montauk Point Lighthouse (photo: James Kirkikis)

For those who want to truly escape, 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. But most famous is the Montauk Point Lighthouse, which has been preserved as a museum. According to the museum’s website, it’s the 4th-oldest operational lighthouse in the entire country and was commissioned by George Washington in 1792.

Greenport

Black Llama Bar at the American Beech Hotel

For something truly unexpected, discover Long Island’s up-and-coming community of Greenport. The town is becoming known for its excellent and trendy lodging and dining options, like the American Beech Hotel, a stunning resort located in downtown Greenport. With modern and stylish rooms and numerous (and very popular) bars and restaurants with both indoor and outdoor seating, you’ll feel more like you’re in Miami than Long Island.

Greenport’s downtown is loaded with restaurants and bars, and the community has its own vineyard, Kontokosta winery. One of Greenport’s hottest spots is Claudio’s, which hosts both a main restaurant and a waterfront property in the town. Claudio’s is a seafood restaurant with ample outdoor seating and live music. Known for their fresh oysters, shrimp scampi, and lobster rolls, diners get stunning views of the harbor, while also being able to listen to some fantastic music. At Claudio’s many diners come for the food, but stay for the great cocktails and live performances. Even cooler, Claudio’s also has a long and fascinating history as a speakeasy. During prohibition, they greeted diners with a formal restaurant downstairs, and a secret upstairs lounge that served boozy libations and provided the night’s most memorable moments.