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 Meschutt 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: 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 Kismet Beach, stroll through Ocean Beach, and take in the waterfront activity at Sailors Haven Visitor Center.

For ratings, more things to do, photos, and more tourist information, read Fire Island trip planner.

New York City to Fire Island is an approximately 2-hour car ride. Expect a daytime high around 84°F in July, and nighttime lows around 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 · Beaches · Outdoors · 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: Orient Beach State Park (in Orient), Quogue Wildlife Refuge (in Quogue) and Wertheim National Wildlife Refuge (in Shirley). There's lots more to do: learn about winemaking at The Old Field Vineyards, explore the different monuments and memorials at Calverton National Cemetery, and tour the pleasant surroundings at Elizabeth A. Morton National Wildlife Refuge.

To see photos, maps, traveler tips, and more tourist information, read our Cutchogue road trip planning tool.

Drive from Fire Island to Cutchogue in 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. Cap off your sightseeing on the 9th (Sun) early enough to 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: tee off at Montauk Downs State Park Golf Course, admire the majestic nature at Montauk Downs State Park, indulge your thirst for a good beer at Montauk Brewing Company, and kick back and relax at Gin Beach.

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 Queens County Farm Museum. Explore the numerous day-trip ideas around Huntington: St. James General Store (in Saint James), Long Island Maritime Museum (in West Sayville) and Corey Beach (in Blue Point). And it doesn't end there: immerse yourself in nature at Sunken Meadow State Park, contemplate the long history of William Floyd Estate, stroll through Joel L. Lefkowitz Park at West Meadow Beach, and enjoy the sand and surf at Lido Beach.

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.