8 days in Long Island Itinerary

8 days in Long Island Itinerary

Created using Inspirock Long Island trip itinerary builder
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Make it your trip
Fly to John F Kennedy International Airport, Drive to Greenport
1
Greenport
— 2 nights
Drive
2
Montauk
— 3 nights
Drive
3
Garden City
— 2 nights
Drive to John F Kennedy International Airport, Fly to Washington

S M T W T F S
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Greenport — 2 nights

Nestled on the north fork of Long Island within a pastoral landscape of farms and vineyards, Greenport is a historic village best known for its waterfront walkway with a 36-horse vintage carousel as its centerpiece.
Relax by the water at Cupsogue Beach County Park and Pike's Beach. Discover out-of-the-way places like Quogue Wildlife Refuge and William Floyd Estate. Step out of Greenport to go to Laurel and see Laurel Lake Vineyard, which is approximately 32 minutes away. The adventure continues: identify plant and animal life at Elizabeth A. Morton National Wildlife Refuge, do a tasting at McCall Wines, visit a coastal fixture at Horton Point Lighthouse Nautical Museum, and get outside with Outdoor Activities.

Inspirock's itinerary builder makes planning a Greenport trip simple and quick.

Washington to Greenport is an approximately 6-hour combination of flight and car. You can also drive. When traveling from Washington in July, plan for a bit cooler days in Greenport, with highs around 79°F, while nights are about the same with lows around 67°F. Wrap up your sightseeing on the 7th (Thu) to allow time to drive to Montauk.
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Wineries · Parks · Outdoors · Historic Sites
Side Trips

Montauk — 3 nights

Montauk is a census-designated place (CDP) that includes the hamlet with the same name located in the town of East Hampton in Suffolk County, New York, on the eastern end of the South Shore of Long Island. You'll explore the less-touristy side of things at Montauk Point State Park and The Leiber Collection. We've included these beaches for you: Gin Beach and Ditch Plains. You'll find plenty of places to visit near Montauk: South Fork Natural History Museum (in Bridgehampton) and Sag Harbor (Foster Memorial Beach & Sag Harbor Whaling and Historical Museum). Next up on the itinerary: play a few rounds at Montauk Downs State Park Golf Course, enjoy the sand and surf at Amsterdam Beach Preserve, gear up at Hampton Beach Service, and visit a coastal fixture at Montauk Point Lighthouse.

For traveler tips, reviews, other places to visit, and tourist information, use the Montauk online holiday builder.

Getting from Greenport to Montauk by car takes about 2 hours. In July, plan for daily highs up to 80°F, and evening lows to 68°F. Finish your sightseeing early on the 10th (Sun) so you can drive to Garden City.
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Outdoors · Parks · Beaches · Museums
Side Trips

Garden City — 2 nights

Garden City is an incorporated village in the town of Hempstead, in central Nassau County, New York, in the United States. Kick off your visit on the 11th (Mon): head off the coast to Fire Island National Seashore, then kick back and relax at Corey Beach, then admire the majestic nature at Connetquot River State Park Preserve, and finally stroll around Joel L. Lefkowitz Park at West Meadow Beach. Get ready for a full day of sightseeing on the next day: take an in-depth tour of Sagamore Hill National Historic Site, steep yourself in history at American Airpower Museum, enjoy the sand and surf at Jones Beach State Park, then enjoy the sand and surf at Lido Beach, and finally kick back and relax at Long Beach.

Plan my day in Garden City using traveler tips and tourist information provided by Inspirock.

Getting from Montauk to Garden City by car takes about 2 hours. Other options: drive. Expect a daytime high around 85°F in July, and nighttime lows around 71°F. Cap off your sightseeing on the 12th (Tue) early enough to go by car back home.
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Parks · Outdoors · Beaches · Nature
Side Trips

Long Island travel guide

4.4
Wineries & Vineyards · Beaches · Lighthouses
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.
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