16 days in Long Island Itinerary

16 days in Long Island Itinerary

Created using Inspirock Long Island visit planner

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Make it your trip
Drive
1
Montauk
— 4 nights
Drive
2
Cutchogue
— 4 nights
Drive
3
Fire Island
— 4 nights
Drive
4
Garden City
— 3 nights
Drive

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Montauk

— 4 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. Get out of town with these interesting Montauk side-trips: LongHouse Reserve (in East Hampton), Wolffer Estate Vineyard (in Sagaponack) and Bridgehampton (Children's Museum of The East End & Channing Daughters Winery). And it doesn't end there: enjoy the sea views from Montauk Point Lighthouse, contemplate the long history of Pollock-Krasner House and Study Center, enjoy the sand and surf at Ditch Plains, and pause for some serene contemplation at St. Therese of Lisieux Catholic Church.

For ratings, more things to do, other places to visit, and tourist information, refer to the Montauk trip builder site.

New York City to Montauk is an approximately 2.5-hour car ride. You can also take a bus; or take a train. In November, daily temperatures in Montauk can reach 54°F, while at night they dip to 42°F. Cap off your sightseeing on the 19th (Thu) early enough to go by car to Cutchogue.

Things to do in Montauk

Parks · Historic Sites · Nature · Outdoors

Side Trips

Cutchogue

— 4 nights
Cutchogue is a hamlet and census-designated place (CDP) in Suffolk County, New York, United States. When in Cutchogue, make a side trip to see Tanger Outlets Riverhead in Riverhead, approximately Riverhead away. And it doesn't end there: get up close and personal with brilliant marine life at Long Island Aquarium, learn about winemaking at Castello di Borghese / Hargrave Vineyard, awaken your taste buds at some of the top wineries in the area, and look and learn at Custer Institute & Observatory.

To find photos, more things to do, other places to visit, and more tourist information, go to the Cutchogue tour itinerary planner.

You can drive from Montauk to Cutchogue in 1.5 hours. In November in Cutchogue, expect temperatures between 51°F during the day and 40°F at night. Wrap up your sightseeing on the 23rd (Mon) to allow time to drive to Fire Island.

Things to do in Cutchogue

Wineries · Shopping · Tours · Zoos & Aquariums

Side Trips

Fire Island

— 4 nights
Fire Island is the large center island of the outer barrier islands parallel to the south shore of Long Island, New York. Get out of town with these interesting Fire Island side-trips: Hampton Bays (House of Wellness & Ponquogue Beach), Water Mill (Duck Walk Vineyard & Parrish Art Museum) and Southampton (Cooper's Beach & Southampton Arts Center). There's much more to do: visit a coastal fixture at Fire Island Lighthouse, look for all kinds of wild species at Sailors Haven Visitor Center, and immerse yourself in nature at Robert Moses State Park.

Planning Fire Island trip won't be overwhelming when you use Inspirock's itinerary maker.

Traveling by car from Cutchogue to Fire Island takes 2 hours. In November, daytime highs in Fire Island are 55°F, while nighttime lows are 37°F. Wrap up your sightseeing on the 27th (Fri) early enough to drive to Garden City.

Things to do in Fire Island

Parks · Wildlife · Beaches · Outdoors

Side Trips

Garden City

— 3 nights
Garden City is an incorporated village in the town of Hempstead, in central Nassau County, New York, in the United States. Get out of town with these interesting Garden City side-trips: Sagamore Hill National Historic Site (in Oyster Bay), Avalon Park & Preserve (in Stony Brook) and Tanger Outlets Deer Park (in Deer Park). And it doesn't end there: examine the collection at Cradle of Aviation Museum, immerse yourself in nature at Sunken Meadow State Park, browse the different shops at Roosevelt Field, and explore the engaging exhibits at Long Island Children's Museum.

To see reviews, ratings, maps, and more tourist information, you can read our Garden City tour itinerary builder.

Getting from Fire Island to Garden City by car takes about 1.5 hours. In November, daytime highs in Garden City are 55°F, while nighttime lows are 40°F. Finish your sightseeing early on the 30th (Mon) to allow enough time to drive back home.

Things to do in Garden City

Parks · Museums · Shopping · Nature

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.