29 days in Long Island Itinerary

29 days in Long Island Itinerary

Created using Inspirock Long Island trip planner

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Make it your trip
Drive
1
Fire Island
— 5 nights
Drive
2
Cutchogue
— 8 nights
Drive
3
Montauk
— 8 nights
Drive
4
Huntington
— 7 nights
Drive

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Fire Island

— 5 nights
Fire Island is the large center island of the outer barrier islands parallel to the south shore of Long Island, New York. Step out of the city life by going to Robert Moses State Park and Kismet Beach. Satisfy your inner culture vulture at Fire Island Lighthouse and Our Lady of Poland Catholic Church. Explore the numerous day-trip ideas around Fire Island: Meschutt Beach (in Hampton Bays), Southampton (Shinnecock East County Park, Hildreth's, &more) and Water Mill (Duck Walk Vineyard & Hank's Pumpkintown). There's still lots to do: delve into the lush surroundings at The Sunken Forest, kick back and relax at Ocean Beach, and go for a stroll along the water at Sailors Haven Visitor Center.

To see where to stay, maps, reviews, and other tourist information, read our Fire Island trip website.

New York City to Fire Island is an approximately 2-hour car ride. In July, daytime highs in Fire Island are 84°F, while nighttime lows are 69°F. Finish your sightseeing early on the 1st (Sat) to allow enough time to drive to Cutchogue.

Things to do in Fire Island

Parks · Outdoors · Beaches · Nature

Side Trip

Cutchogue

— 8 nights
Cutchogue is a hamlet and census-designated place (CDP) in Suffolk County, New York, United States. Shop till you drop at Alex Ferrone Gallery and North Fork Chocolate Company. Appreciate the collections at Horton Point Lighthouse Nautical Museum and Oysterponds Historical Society. Explore the numerous day-trip ideas around Cutchogue: Quogue Wildlife Refuge (in Quogue), Orient Beach State Park (in Orient) and Wertheim National Wildlife Refuge (in Shirley). And it doesn't end there: do a tasting at The Old Field Vineyards, stroll the grounds of Calverton National Cemetery, stroll through Elizabeth A. Morton National Wildlife Refuge, and head outdoors with Outdoor Activities.

To find reviews, other places to visit, traveler tips, and other tourist information, read Cutchogue trip itinerary planning app.

Traveling by car from Fire Island to Cutchogue takes 2 hours. Expect slightly colder weather when traveling from Fire Island in August: highs in Cutchogue hover around 77°F, while lows dip to 64°F. Finish up your sightseeing early on the 9th (Sun) so you can go by car to Montauk.

Things to do in Cutchogue

Wineries · Parks · Wildlife · Historic Sites

Side Trips

Montauk

— 8 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 outdoors at Shadmoor State Park and Foster Memorial Beach. Pollock-Krasner House and Study Center and Guild Hall are good opportunities to explore the local culture. Venture out of the city with trips to Home Sweet Home Museum (in East Hampton), Bridgehampton (Children's Museum of The East End, Channing Daughters Winery, &more) and Sag Harbor (Sag Harbor Marine Park, Sag Harbor Whaling and Historical Museum, &more). And it doesn't end there: enjoy the sand and surf at Kirk Park Beach, admire the majestic nature at Montauk Downs State Park, stroll around Navy Road Park, and see the interesting displays at The Leiber Collection.

To find ratings, photos, more things to do, and tourist information, refer to the Montauk online road trip planner.

You can drive from Cutchogue to Montauk in 1.5 hours. August in Montauk sees daily highs of 79°F and lows of 66°F at night. Finish your sightseeing early on the 17th (Mon) to allow enough time to travel to Huntington.

Things to do in Montauk

Parks · Museums · Outdoors · Beaches

Side Trips

Huntington

— 7 nights
The Town of Huntington is one of ten towns in Suffolk County, New York, United States. Take a break from the city and head to Sands Point Preserve and Tobay Beach. Get some historical perspective at Old Bethpage Village Restoration and William Floyd Estate. Explore the numerous day-trip ideas around Huntington: Corey Beach (in Blue Point), Long Island Maritime Museum (in West Sayville) and St. James General Store (in Saint James). And it doesn't end there: contemplate the long history of Queens County Farm Museum, pause for some photo ops at Argyle Park, kick back and relax at Lido Beach, and tee off at Bethpage Black.

To find where to stay, more things to do, other places to visit, and other tourist information, go to the Huntington trip planner.

Getting from Montauk to Huntington by car takes about 2 hours. In August, daytime highs in Huntington are 82°F, while nighttime lows are 67°F. Finish your sightseeing early on the 24th (Mon) to allow enough time to drive back home.

Things to do in Huntington

Parks · Outdoors · Historic Sites · Beaches

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.