Discover and Explore Long Island

Long Island



Anchored in the Atlantic Ocean just southeast of New York City is the East Coast gem of Long Island. Though perhaps best known for its vineyards and vast array of lavish summer vacation rental homes, Long Island is not only a haven for the celebrated rich and famous. With its wealth of white-sand beaches, sky-high surf and Eastern coastal charm, both shores of Long Island attract flocks of regulars and tourists alike, particularly in the warmer months. Set apart by its distinct blue, green and white color palate, Long Island is a summer vacation destination with a long nautical history, perfect for the seafaring soul.


Long Island Areas:

  • Orient Point - Is perched on the very northern tip of the North Fork of Long Island. Accessible by automobile but most frequently by ferry from New London across the Sound, Orient is a sleepy but whimsical community best appreciated on the beach; rent a kayak or just relax on the sand to enjoy one of the most solitary stretches of shore in the area. Even if you’re just passing through, don’t forget to stop at Four & Twenty Blackbirds; this tiny Brooklyn-transplanted bakery makes the best pies anywhere on the island. Another treat, just five minutes down the road in neighboring East Marion, is the gorgeous flower farm Lavender by the Bay, which sells its aromatic stems year-round but is best observed in bloom from late June through early July. 
  • Greenport - Hailed by Forbes as one of the prettiest towns in America, Greenport proudly parades its nautical heritage amidst its charming inns and renowned wineries. Though trendy coffee shops and art galleries betray the Manhattanite clientele, this town’s summer cottages and pebbles beaches retain the essence of the 19th-century fishing village, and a golden-age brass ring carousel stands as one of Greenport’s treasured attractions. Dine at the Frisky Oyster for inarguably the most outstanding cuisine in the area, but you won’t be steered wrong by any of the farm-fresh restaurants along the harbor on Front and Main. 
  • Cutchogue -  Is a vital stop on any North Fork wine tour, as it is home not only to picturesque cottages and small white churches but also to the oldest established winery on Long Island: Castello de Borghese/Hargrave Vineyard, operating since 1973. In fact, Cutchogue is home to nearly a dozen wineries, each with unique offerings, tastings, and tours.
  • Shelter Island -Nestled between the North and South Forks, you’ll find Shelter Island, reachable from both the North and South forks via ferry. Cars are also welcome aboard the ferry and on the island but are by no means necessary to enjoy the secluded beauty of the area. Part nature preserve, part sunset-ready beaches and part scenic getaway vacation rentals, this magical “island between islands” gives a taste of Hamptons glamour, minus the crowds. For some dynamic local flavor, attend the Wednesday night barbeque on the front lawn of the Pridwin: this picturesque ocean-side bake is a cherished seasonal ritual.
  • Fire Island - Is a strip barrier island protecting the south shore of Long Island from the open ocean. Accessible primarily by ferry or boat, Fire Island is best navigated on foot or bicycle: vehicular traffic is prohibited during peak summer months. Host to several vibrant LGBT communities, the 32 miles of this island strip are also dotted with close-knit private towns, camping spots, family-friendly vacation areas, and several state parks. Spend the day exploring the Sunken Forest, then walk the beach to dine in charming Ocean Beach; whether you seek the pastoral comfort of the western end or the festive revelry of the east, Fire Island offers an escape from the rush of modern life. 
  • Hamptons - Of course, the much-acclaimed crown jewels of Long Island are the Hamptons—West, East, South, and Bridge—each as diverse as they are exclusive.
    • Extravagant East Hampton is home to the upscale, glossy crowds and is the place to see and be seen, as well as the place to casually run into resident celebrities at the local coffee shops.
    • Drive through Southampton to catch a glimpse of luxurious mansions over well-groomed hedges, spend some time shopping the high-end storefronts on Main St and enjoy a refreshing gelato.
    • Over in Bridgehampton, you’ll find unique boutiques and antique shops, as well as a thriving equestrian community; this village hosts the annual Hampton Classic Horse Show and polo matches every summer.
    • Westhampton, with its heady party scene and swelling numbers of summer rental visitors, boasts some of the most beautiful beachfront on the East Coast. 
  • Sag Harbor - Located within the districts of East and Southampton, Sag Harbor’s rich history as an old whaling port gives it a distinctly rustic charm. With many of the buildings listed on the National Register of Historic Places, this village retains its vintage New England vibe and provides a relaxing alternative to the powerful energy of its neighboring towns. Much of Sag Harbor’s attractions line a quarter-mile stretch of Main Street near the bay, a veritable treasure trove of quaint stores and restaurants. While lacking the gorgeous beaches of the rest of the Hamptons, the namesake deep-water harbor plays perfect host to yacht races and chartered sailing. For an extra dose of preserved history, visit the “Umbrella House,” rumored to be the oldest home in the area, which hosted British soldiers during the war of 1812 and now houses a local wine and cheese shop.
  • Montauk - Montauk Point Light House, commissioned by George Washington in 1792, stands at the southeastern tip of Long Island and remains the pride and joy of its windswept namesake, Montauk. Despite its proximity to both the Hamptons and wine-country, this surf-shack town feels a world away from its elite neighbors and attracts a more laid-back population of fishers, beachcombers and, of course, surfers. True to its roots as a fishing village, Montauk’s restaurants offer an array of fresh New England catches with a side of the authentic, relaxed vibe that sets this town apart from its comrades. Head to Ditch Plains for incredible surf waves, and visit the lighthouse at dusk for an incredible view of the sunset.


Things to Do

  • Swimming
  • Surfing
  • Boating
  • Kayaking
  • Paddle-boarding
  • Beachcombing
  • Oyster shucking
  • Wine trail tours (guided or self-guided)
  • Shopping
  • Antiquing
  • Horseback Riding
  • Montauk Point Lighthouse
  • Fire Island Lighthouse
  • Long Island Maritime Museum
  • Long Island Aquarium
  • Sag Harbor Whaling Museum
  • Southampton Arts Center
  • Splish Splash, Long Island’s largest water park (can be crowded)
  • Tanger Outlets in Riverhead
  • Take a day trip to NYC

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  • Car: Long Island is accessible via several major highways, but be sure to allow time if you choose to drive. Traffic, especially on weekends, can be brutal.
  • Air: JFK Airport (located in Queens, NY) and Islip MacArthur Airport (ISP) are the closest major airports to Long Island. However, if traveling by private plane, Republic Airport in Farmingdale or Gabreski Airport in Westhampton Beach may also be options.
  • Train: The Long Island Railroad (LIRR) has a line that operates from Penn Station all the way out to Montauk.
  • Bus: The Hampton Jitney bus runs regularly from New York City to both the North and South forks of Long Island.
  • Ferry: If you’re coming from the north, the ferry from New London, CT usually offers a faster way to beat the traffic. For an additional fee, you can bring your car on board with you so you’ll be ready to hit the road upon docking.

Upon Arrival:

  • Taxi: There are a number of taxi companies servicing the Long Island area, as well as other car services such as Uber and Lyft.
  • Bus: Suffolk County Transportation services routes along the shore and the North and South forks, but can be a slower option.
  • Trolley: A new trolley program premiered in Fall 2017, intended to alleviate traffic and shuttle up to 30 visitors per trolley to various destinations along the North Fork, from Mattituck to Greenport.
  • Bicycle: Cycling is a popular mode of transportation across shorter distances and are often available for rent at inns and private companies.



Though Long Island has a sizeable four-season population, the island’s numbers swell from May to October during the summer term. Making the warmer months the ideal time to book and discover the best Long Island vacation rentals.

In the cooler months, many visitors retreat back to New York City and other permanent residences, leaving a quiet, sometimes ghostly beachfront in their wake. Winter can be a devastatingly beautiful time to visit the Long Island coast, bringing snowy beaches and crackling fireplaces; however, undeniably, summer is the liveliest of all the seasons for any of these shoreline towns.

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