8 days in Long Island Itinerary

8 days in Long Island Itinerary

Created using Inspirock Long Island tour itinerary planner

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Make it your trip
Fly to John F Kennedy International Airport, Drive to Garden City
1
Garden City
— 2 nights
Drive
2
Montauk
— 2 nights
Drive
3
Riverhead
— 3 nights
Drive to John F Kennedy International Airport, Fly to Raleigh Durham International Airport

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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. Venture out of the city with trips to Sagamore Hill National Historic Site (in Oyster Bay) and Tanger Outlets Deer Park (in Deer Park). There's much more to do: examine the collection at Cradle of Aviation Museum, admire the natural beauty at Planting Fields Arboretum State Historic Park, stop by Jericho Cider Mill, and indulge in some personalized pampering at Port Salt Cave.

To see maps, traveler tips, other places to visit, and more tourist information, read our Garden City trip planner.

Durham to Garden City is an approximately 4.5-hour combination of flight and car. You can also drive. Plan for a bit cooler temperatures traveling from Durham in March, with highs in Garden City at 47°F and lows at 33°F. Finish your sightseeing early on the 1st (Thu) to allow enough time to travel to Montauk.

Things to do in Garden City

Museums · Parks · Wildlife · Historic Sites

Side Trips

Montauk

— 2 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. Start off your visit on the 2nd (Fri): immerse yourself in nature at Montauk Point State Park, then visit a coastal fixture at Montauk Point Lighthouse, and then make a trip to Gosman's Restaurant. Keep things going the next day: get engrossed in the history at Custom House Museum, then get a new perspective on things with Boat Tours & Water Sports, then do a tasting at Wolffer Estate Vineyard, and finally admire the majestic nature at Hither Hills State Park.

To see photos, ratings, maps, and more tourist information, use the Montauk day trip website.

Traveling by car from Garden City to Montauk takes 2 hours. In April, daily temperatures in Montauk can reach 55°F, while at night they dip to 41°F. Finish up your sightseeing early on the 3rd (Sat) so you can go by car to Riverhead.

Things to do in Montauk

Parks · Nature · Outdoors · Historic Sites

Side Trips

Riverhead

— 3 nights
Riverhead is a town within Suffolk County, New York, on the north shore of Long Island. Get out of town with these interesting Riverhead side-trips: Kontokosta Winery (in Greenport) and Mattebella Vineyards (in Southold). There's much more to do: observe the fascinating underwater world at Long Island Aquarium, do a tasting at Sannino Bella Vita Vineyard, indulge your senses at some of the top wineries in the area, and take in the exciting artwork at Alex Ferrone Gallery.

To see ratings, reviews, traveler tips, and tourist information, you can read our Riverhead road trip app.

You can drive from Montauk to Riverhead in 1.5 hours. Traveling from Montauk in April, plan for little chillier nights in Riverhead, with lows around 35°F. Finish your sightseeing early on the 6th (Tue) to allow enough time to travel back home.

Things to do in Riverhead

Wineries · Tours · Zoos & Aquariums · Parks

Side Trips

Long Island travel guide

4.3
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.