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Long Island trip planner
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itinerary for free
Long Island
Stretching northeast from New York Harbor to the Atlantic Ocean, Long Island is the largest island in the continental U.S. It technically includes the New York City boroughs of Brooklyn and Queens, but generally refers to the suburban counties of Nassau and Suffolk exclusively. Known for its cookie-cutter suburban neighborhoods, the island is also home to a wealth of intriguing places to visit, including beaches, scenic countryside, wineries, and numerous historical sites. In the summer months, wealthy New Yorkers flock here to relax in their exclusive Hamptons properties. Our United States route planner combines visitor reviews with your personal interests to make an itinerary informed by experts, but tailored to suit your style.
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Top Long Island tours
Places to visit in Long Island
MontaukTrip planner
Best for: Lighthouse, Dolphin / Whale Watching, Fishing Charter / Tour
RiverheadTrip planner
Best for: Aquarium, Winery / Vineyard, Factory Outlet
GreenportTrip planner
Best for: Wine Tour / Tasting, Winery / Vineyard, Theme Park
SouthamptonTrip planner
Best for: Beach, Art Museum, Winery / Vineyard
Sag HarborTrip planner
Best for: Theater, Specialty Museum, Beach
Regions of Long Island
Wineries in Long Island
Parks in Long Island
Hidden gems in Long Island
Where to stay in Long Island

Browse hotels, guesthouses, and unique homes and book your stay on the world's leading accommodation sites.
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Recently planned trips to Long Island
7 days in Huntington
BY A USER FROM UNITED KINGDOM
Wine Tours & Tastings
Boat Tours & Water Sports
Jones Beach State Park
9 days in Hamptons
BY A USER FROM UNITED STATES
Riverhead
Shelter Island
Montauk
3 days in Southold
BY A USER FROM UNITED STATES
Wine Tours & Tastings
Sparkling Pointe Vineyards & Winery
Custer Institute & Observatory
2 days in Cedarhurst
BY A USER FROM UNITED STATES
Freeport's Nautical Mile
Fishing Charters & Tours
Long Beach
5 days in Long Island
BY A USER FROM UNITED STATES
Bayville
Southampton
5 days in East Hampton
BY A USER FROM UKRAINE
Havens Beach
Mashomack Preserve
Boat Tours & Water Sports
12 days in New York City & Montauk
BY A USER FROM UNITED STATES
New York City
Montauk
8 days in East Hampton
BY A USER FROM UNITED STATES
Sylvester Manor Educational Farm
Mashomack Preserve
Havens Beach
11 days in Greenport
BY A USER FROM UNITED STATES
Camera Obscura
East End Seaport Maritime Museum
Virgin Star Sailing Adventures
1 day in Montauk
BY A USER FROM UNITED STATES
Main Beach
Ditch Plains
Dolphin & Whale Watching
3 days in Long Island
BY A USER FROM UNITED STATES
Southampton
1 day in Fire Island
BY A USER FROM UNITED STATES
Robert Moses State Park
Fire Island Lighthouse
Fire Island Parasail