22 days in Long Island Itinerary

22 days in Long Island Itinerary

Created using Inspirock Long Island journey planner

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Make it your trip
Drive
1
Montauk
— 6 nights
Drive
2
Cutchogue
— 8 nights
Drive
3
Fire Island
— 7 nights
Drive

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Montauk

— 6 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. Sag Harbor Whaling and Historical Museum and The Leiber Collection will appeal to museum buffs. Eschew the tourist crowds and head to Montauk Point State Park and Main Beach. Get out of town with these interesting Montauk side-trips: Bridgehampton (South Fork Natural History Museum, Channing Daughters Winery, &more), Sag Harbor (Foster Memorial Beach & Custom House Museum) and East Hampton (Guild Hall & Home Sweet Home Museum). Next up on the itinerary: play a few rounds at Montauk Downs State Park Golf Course, steep yourself in history at Pollock-Krasner House and Study Center, immerse yourself in nature at Montauk Downs State Park, and browse the fresh offerings at Round Swamp Farm.

To find ratings, traveler tips, reviews, and tourist information, go to the Montauk road trip planning website.

New York City to Montauk is an approximately 2.5-hour car ride. You can also take a bus; or take a train. In August, Montauk is a bit cooler than New York City - with highs of 79°F and lows of 66°F. Finish your sightseeing early on the 15th (Sat) so you can drive to Cutchogue.

Things to do in Montauk

Museums · Parks · Outdoors · Nature

Side Trips

Cutchogue

— 8 nights
Cutchogue is a hamlet and census-designated place (CDP) in Suffolk County, New York, United States. You'll discover tucked-away gems like Boat Tours & Water Sports and Alex Ferrone Gallery. Long Island Maritime Museum and Oysterponds Historical Society will appeal to museum buffs. Venture out of the city with trips to Corey Beach (in Blue Point), Organics Today Farm (in East Islip) and Orient Beach State Park (in Orient). There's still lots to do: stroll through Elizabeth A. Morton National Wildlife Refuge, do a tasting at Osprey's Dominion Vineyards, kick back and relax at Pike's Beach, and visit a coastal fixture at Horton Point Lighthouse Nautical Museum.

To see more things to do, photos, ratings, and more tourist information, read Cutchogue itinerary planning site.

Traveling by car from Montauk to Cutchogue takes 1.5 hours. In August, daily temperatures in Cutchogue can reach 77°F, while at night they dip to 64°F. Wrap up your sightseeing on the 23rd (Sun) early enough to drive to Fire Island.

Things to do in Cutchogue

Wineries · Parks · Outdoors · Beaches

Side Trips

Fire Island

— 7 nights
Fire Island is the large center island of the outer barrier islands parallel to the south shore of Long Island, New York. Sagamore Hill National Historic Site and Parrish Art Museum will appeal to museum buffs. You'll explore the less-touristy side of things at Long Beach and Ponquogue Beach. Venture out of the city with trips to St. James General Store (in Saint James), Hampton Bays (House of Wellness & Meschutt Beach) and Museum of American Armor (in Old Bethpage). There's much more to do: glide through the air with Fire Island Parasail, tour the pleasant surroundings at Shinnecock East County Park, immerse yourself in nature at Sunken Meadow State Park, and enjoy the sand and surf at Kismet Beach.

To see where to stay, other places to visit, more things to do, and tourist information, use the Fire Island trip planner.

Traveling by car from Cutchogue to Fire Island takes 2 hours. In August, plan for daily highs up to 82°F, and evening lows to 66°F. Wrap up your sightseeing on the 30th (Sun) early enough to drive back home.

Things to do in Fire Island

Parks · Outdoors · Beaches · 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.