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Home to New York's most sought-after waterfront destinations, Long Island provides everything a boater could desire. White-sand beaches and tranquil bays complement charming town centers and ritzy restaurants perfectly. Famous for its high-profile seaside havens like the Hamptons, Long Island is best appreciated by boat. There’s a bounty to discover while cruising the island’s 1,600- mile coastline — teeming with fish and dotted with inviting marinas, fetching beach towns, flavorsome vineyards and exclusive shopping.
Framed by the Long Island Sound to the North and the Atlantic Ocean to the South, Long Island extends west-to-east from Manhattan’s East River to Montauk Point. It’s the largest island in the contiguous United States, extending over 118 miles long and up to 23 miles wide. Elegant architecture, world-class dining and luxurious accommodations have drawn vacationers here for more than a century. The following nine Long Island destinations belong on every boater’s must-visit list:
Tree-lined streets with alluring gift shops, stately historic homes and a lively restaurant scene define this oceanfront hamlet on Long Island’s North Shore. Port Washington’s beaches, parks and wellness retreats make this charismatic village an excellent place for some quality R&R. Relish a spa day or enjoy a leisurely lunch while gazing upon the harbor dotted with yachts and sailboats. This coastal community was originally founded as a sand-mining town in the late 19th century and later became a hub for boats out of New York City. Many of the historic buildings remain today, such as the Sands Point Preserve on the original Guggenheim Estate. Located about 20 miles from New York City, Port Washington presents an ideal entry or exit point for boating city-goers.
Where to Dock: Safe Harbor Capri or North Hempstead Town Dock
This mile-long bay and welcoming waterfront village on the North Shore of Long Island was first settled in 1653, its neighboring harbors serving as access points to Long Island’s interior farmlands. Huntington Bay’s architectural uniqueness is thanks in part to August Heckscher, a German-born philanthropist who financed many of Huntington’s homes and built the Heckscher Museum of Art and Heckscher Park. A section of Long Island’s “Gold Coast,” a nickname earned by the affluent communities on its northern shores, Huntington Bay offers exquisite mansions to ogle over, paired with idyllic streets lined with boutique eateries and shops.
Where to Dock: West Shore Marina
Friendly parks and beaches on Long Island’s northern shore along with stunning views of the Long Island Sound can be found in Port Jefferson. Cultural attractions like the Historical Society and Long Island Explorium, a nautical- themed museum with hands-on activities for kids, make this former ship-building town fun for the whole family. Boat enthusiasts can check out Bayles Boat Shop, where visitors learn about building and restoring wooden boats. One of just two ports on Long Island with access from Connecticut, Port Jefferson has become a top boating destination with fantastic restaurants, festivals and year-round live theater.
Where to Dock: Danfords Hotel, Marina & Spa
Along the Peconic River in the lush greenery of Long Island’s East End, Riverhead bestows ample ways to adventure. Kayak the river, attend a local event such as the annual cardboard boat race (early August) or catch the thrill of a car race at Riverhead Raceway. Riverhead’s Long Island Aquarium boasts one of the largest coral reefs in the world, and Jamesport Brewery invites visitors to taste freshly brewed beer made with homegrown hops and barley. In addition to photogenic farms, vineyards and beaches, delectable eateries abound in Riverhead’s historic downtown area.
Where to Dock: Treasure Cove Resort Marina
Opulent estates, endless beaches and a provocative art scene describe this hamlet on Long Island’s southeastern shore. Noted today for its relaxed surfy vibe among Hamptons hot spots, the village of East Hampton was originally settled by Puritan farmers in the 17th century. Between taking long beach walks and eating world-class food, get inspired at the Pollock-Krasner House, an art museum and the former residence of artists Jackson Pollock and his wife Lee Krasner. Catch an exhibit or show at Guild Hall, a museum, performing arts and education center founded in 1931. Also worth a visit while in East Hampton, the stunning gardens and outdoor sculpture gallery at LongHouse Reserve are sure to leave the whole family breathless.
Where to Dock: Halsey’s Marina or Three Mile Harbor Marina
Between the North and South Forks, the two peninsulas Long Island tapers into at its East End, lies Shelter Island — home to century-old inns, a nature preserve, bikeable roads and exhilarating hikes. The 29-square-mile island is only accessible by boat or ferry, creating a secluded feel for visitors who come to paddleboard, golf the island’s nine-hole course, peruse organic markets, yacht-watch while dining alfresco, savor wine at local vineyards or sun themselves on tranquil beaches. Step back in time at the Shelter Island Historical Society or traverse within the 2,100-acre Mashomack Preserve.
Where to Dock: Piccozzi’s Dering Harbor Marina or Coecles Harbor Marina & Boatyard
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This amiable North Fork seaport village is renowned for vintage shopping, spectacular golf courses, hip restaurants, boutique hotels and award-winning vineyards. At this former whaling and railroad town, visitors can discover Long Island’s seafaring and shipbuilding past at the East End Seaport Maritime Museum or bone up on train lore at the Railroad Museum of Long Island. Encircled by the picturesque Greenport and Stirling Harbors, the waterfront town center spotlights an iconic 100-year-old antique carousel in the heart of Mitchell Park. Just a short drive or boat ride from Greenport, at the tip of the North Fork, lies Orient Point. Its coffee-pot-shaped lighthouse adorns panoramic views of the Long Island Sound and Gardiners Bay.
Where to Dock: Mitchell Park Marina, Townsend Manor Inn and Marina, or Safe Harbor Stirling
Split between the towns of East Hampton and Southampton, the village of Sag Harbor bridges the two in incredible fashion. Known for small-town cuteness, choice shopping, delightful restaurants and blissful beaches, Sag Harbor blends its 18th century whaling history with a contemporary low-key feel. After catching your morning buzz at Grindstone Coffee and Donuts, treat yourself to gifts on historic Main Street, trek around Elizabeth Alexandra Morton National Wildlife Refuge or sunbathe at Havens Beach on Sag Harbor Bay. Thanks to the protected bay, Sag Harbor’s beaches tend to have much calmer waters than others in the Hamptons.
Where to Dock: Sag Harbor Yacht Club or Sag Harbor Cove Yacht Club
At the tip of Long Island’s South Fork, Montauk offers surf-friendly beaches, stellar views and a lively downtown. Known as the “end of the world,” New York’s easternmost point started as a fishing village before it became a summer destination for warm- weather beachgoers. Central to Montauk and hosting the Montauk Music Festival each May is the picture- perfect Montauk Point Lighthouse, commissioned by President George Washington in 1792. Behold other panoramas while cruising along the Montauk Highway or climbing the bluffs of Shadmoor State Park, then wash it all down with a beer at Montauk Brewing Company. For a more rustic excursion, saddle up and ride horses along the beach at Deep Hollow Ranch, the oldest working ranch in the United States.
Where to Dock: Safe Harbor Montauk Yacht Club or Montauk Anglers Club & Marina
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