22 days in Long Island Itinerary

22 days in Long Island Itinerary

Created using Inspirock Long Island journey planner

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Plan created by another user. Make it yours

Route & dates

1
Montauk
— 6 nights
2
Cutchogue
— 8 nights
3
Fire Island
— 7 nights

6
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. Sag Harbor Whaling and Historical Museum and Children's Museum of The East End will appeal to museum buffs. Eschew the tourist crowds and head to Montauk Point State Park and Gin Beach. Get out of town with these interesting Montauk side-trips: Sag Harbor (Foster Memorial Beach & Custom House Museum), Bridgehampton (South Fork Natural History Museum & Channing Daughters Winery) and East Hampton (Guild Hall & Home Sweet Home Museum). And it doesn't end there: see majestic marine mammals with Viking Fleet, see the interesting displays at The Leiber Collection, steep yourself in history at Pollock-Krasner House and Study Center, and visit a coastal fixture at Montauk Point Lighthouse.

To see maps, more things to do, reviews, and tourist information, refer to the Montauk tour itinerary builder tool.

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. Wrap up your sightseeing on the 15th (Sat) to allow time to drive to Cutchogue.

Things to do in Montauk

Museums · Outdoors · Parks

Side Trips

East Hampton, Sag Harbor, Bridgehampton
Highlights from your plan
Montauk Downs State Park Golf Course ©
Montauk Downs State Park Golf Course
Main Beach ©
Main Beach
The Leiber Collection ©
The Leiber Collection

8
nights
Cutchogue

Cutchogue ©
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 Raphael Winery. Alex Ferrone Gallery and Long Island Maritime Museum will appeal to museum buffs. Venture out of the city with trips to Organics Today Farm (in East Islip), Corey Beach (in Blue Point) and Orient Beach State Park (in Orient). There's still lots to do: do a tasting at The Old Field Vineyards, kick back and relax at Pike's Beach, look for all kinds of wild species at Elizabeth A. Morton National Wildlife Refuge, and indulge your thirst for a good beer at Greenport Harbor Brewing Co..

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 travel to Fire Island.

Things to do in Cutchogue

Wineries · Parks · Outdoors

Side Trips

Southold, Peconic, Greenport, Orient, Jamesport
Highlights from your plan
Castello di Borghese / Hargrave Vineyard ©
Castello di Borghese / Hargrave Vineyard
Orient Beach State Park ©
Orient Beach State Park
Quogue Wildlife Refuge ©
Quogue Wildlife Refuge

7
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. Sagamore Hill National Historic Site and Southampton Arts Center will appeal to museum buffs. You'll explore the less-touristy side of things at Long Beach and Robert Moses State Park. Venture out of the city with trips to Parrish Art Museum (in Water Mill), St. James General Store (in Saint James) and Hampton Bays (House of Wellness, Meschutt Beach, &more). There's much more to do: enjoy the sand and surf at Ocean Beach, tour the pleasant surroundings at Cooper's Beach, look for all kinds of wild species at Sailors Haven Visitor Center, and admire the majestic nature at Sunken Meadow State Park.

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

Traveling by journey 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 travel back home.

Things to do in Fire Island

Parks · Outdoors · Beaches

Side Trips

Southampton, William Floyd Estate, Sunken Meadow State Park, Sagamore Hill National Historic Site, Museum of American Armor
Highlights from your plan
Robert Moses State Park ©
Robert Moses State Park
Ponquogue Beach ©
Ponquogue Beach
Sagamore Hill National Historic Site ©
Sagamore Hill National Historic Site

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