8 days in Long Island Itinerary

8 days in Long Island Itinerary

Created using Inspirock Long Island trip planner
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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

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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. Take a break from the city and head to Quogue Wildlife Refuge and Boat Tours & Water Sports. Change things up with these side-trips from Greenport: Laurel Lake Vineyard (in Laurel) and William Floyd Estate (in Mastic Beach). And it doesn't end there: look for all kinds of wild species at Elizabeth A. Morton National Wildlife Refuge, visit a coastal fixture at Horton Point Lighthouse Nautical Museum, and learn about winemaking at Coffee Pot Cellars Tasting Room.

For where to stay, traveler tips, reviews, and tourist information, refer to the Greenport trip planner.

Washington to Greenport is an approximately 6-hour combination of flight and car. You can also drive. Traveling from Washington in July, expect nights in Greenport to be about the same, around 67°F, while days are slightly colder, around 79°F. Finish your sightseeing early on the 3rd (Sun) to allow enough time to drive to Montauk.
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Wineries · Parks · Outdoors · Beaches
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. Appreciate the collections at The Leiber Collection and South Fork Natural History Museum. Visiting Montauk Point State Park and Foster Memorial Beach will get you outdoors. Change things up with a short trip to Sag Harbor Whaling and Historical Museum in Sag Harbor (about 36 minutes away). There's lots more to do: get a dose of the wild on Hampton Beach Service, kick back and relax at Amsterdam Beach Preserve, stroll through Ditch Plains, and tee off at Montauk Downs State Park Golf Course.

To find maps, more things to do, reviews, and other tourist information, read our Montauk trip planner.

You can drive from Greenport to Montauk in 2 hours. July in Montauk sees daily highs of 80°F and lows of 68°F at night. Finish up your sightseeing early on the 6th (Wed) so you can go by car 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. Start off your visit on the 7th (Thu): explore the striking landscape of Fire Island National Seashore, enjoy the sand and surf at Corey Beach, then admire the majestic nature at Connetquot River State Park Preserve, and finally enjoy the sand and surf at Joel L. Lefkowitz Park at West Meadow Beach. On your second day here, steep yourself in history at Sagamore Hill National Historic Site, learn about all things military at American Airpower Museum, then enjoy the sand and surf at Jones Beach State Park, then kick back and relax at Lido Beach, and finally kick back and relax at Long Beach.

Plan a Garden City trip in moments using our itinerary builder.

You can drive from Montauk to Garden City in 2 hours. Another option is to drive. In July, daytime highs in Garden City are 85°F, while nighttime lows are 71°F. Wrap up your sightseeing on the 8th (Fri) to allow time to drive back home.
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Parks · Beaches · Outdoors · 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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