29 days in Long Island Itinerary

29 days in Long Island Itinerary

Created using Inspirock Long Island trip planner

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Plan created by another user. Make it yours
1
Fire Island
— 5 nights
2
Cutchogue
— 8 nights
3
Montauk
— 8 nights
4
Huntington
— 7 nights

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5
nights
Fire Island

Fire Island ©
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: Water Mill (Duck Walk Vineyard & Hank's Pumpkintown) and Southampton (Shinnecock East County Park, Hildreth's, &more). There's lots more to do: take a peaceful walk through The Sunken Forest, kick back and relax at Kismet Beach, tour the pleasant surroundings at Ocean Beach, and take in the waterfront activity at Sailors Haven Visitor Center.

To find maps, ratings, photos, and other tourist information, use the Fire Island online trip planner.

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

Things to do in Fire Island

Parks · Outdoors · Beaches · Nature

Side Trip

Highlights from your plan
The Sunken Forest ©
The Sunken Forest
Fire Island Lighthouse ©
Fire Island Lighthouse
Meschutt Beach ©
Meschutt Beach

8
nights
Cutchogue

Cutchogue ©
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). The adventure continues: learn about winemaking at Laurel Lake Vineyard, stroll the grounds of Calverton National Cemetery, get a new perspective on things with Boat Tours & Water Sports, and identify plant and animal life at Elizabeth A. Morton National Wildlife Refuge.

Plan a Cutchogue trip in moments using our itinerary builder.

Travel from Fire Island to Cutchogue in 2 hours. While traveling from Fire Island, expect little chillier days and about the same nights in Cutchogue, ranging from highs of 77°F to lows of 64°F. Wrap up your sightseeing on the 9th (Sun) to allow time to drive to Montauk.

Things to do in Cutchogue

Wineries · Parks · Wildlife · Historic Sites

Side Trips

Highlights from your plan
Raphael Winery ©
Raphael Winery
Quogue Wildlife Refuge ©
Quogue Wildlife Refuge

8
nights
Montauk

Montauk ©
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 Kirk Park Beach. Pollock-Krasner House and Study Center and The Leiber Collection are good opportunities to explore the local culture. Venture out of the city with trips to East Hampton (Home Sweet Home Museum & Guild Hall), Sag Harbor (Foster Memorial Beach, Sag Harbor Marine Park, &more) and Bridgehampton (Children's Museum of The East End, Channing Daughters Winery, &more). There's lots more to do: tee off at Montauk Downs State Park Golf Course, don't miss a visit to St. Therese of Lisieux Catholic Church, take an in-depth tour of Second House Museum, and pick up some local products at Round Swamp Farm.

To find reviews, more things to do, other places to visit, and more tourist information, read our Montauk trip maker website.

Getting from Cutchogue to Montauk by car takes about 1.5 hours. In August, daytime highs in Montauk are 79°F, while nighttime lows are 66°F. Finish up your sightseeing early on the 17th (Mon) so you can travel to Huntington.

Things to do in Montauk

Parks · Museums · Outdoors · Beaches

Side Trips

Highlights from your plan
Montauk Downs State Park Golf Course ©
Montauk Downs State Park Golf Course
The Leiber Collection ©
The Leiber Collection
Guild Hall ©
Guild Hall

7
nights
Huntington

Huntington ©
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 Bethpage Black. Get some historical perspective at Old Bethpage Village Restoration and Argyle Park. 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). There's much more to do: immerse yourself in nature at Belmont Lake State Park, admire the masterpieces at Long Island Museum of American Art, History and Carriages, tour the pleasant surroundings at Joel L. Lefkowitz Park at West Meadow Beach, and browse the exhibits of Queens County Farm Museum.

For reviews, maps, photos, and tourist information, go to the Huntington trip planner.

You can drive from Montauk to Huntington in 2 hours. In August, daytime highs in Huntington are 82°F, while nighttime lows are 67°F. Wrap up your sightseeing on the 24th (Mon) to allow time to drive back home.

Things to do in Huntington

Parks · Outdoors · Historic Sites · Beaches

Side Trips

Highlights from your plan
Sunken Meadow State Park ©
Sunken Meadow State Park
Sands Point Preserve ©
Sands Point Preserve
Long Island Maritime Museum ©
Long Island Maritime Museum

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