43 days in Long Island Itinerary

43 days in Long Island Itinerary

Created using Inspirock Long Island tour planner

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Route & dates

43 days in Long Island Itinerary

Start: New York City
Drive:  1​h 15​min
1
Ronkonkoma
— 9 nights
Drive:  1​h 15​min
2
Ocean Beach, Fire Island
— 10 nights
Drive:  2​h 15​min
3
Montauk
— 11 nights
Drive:  1​h 45​min
4
Greenport
— 12 nights
Drive:  2​h 15​min
End: New York City

9
nights
Ronkonkoma

Ronkonkoma ©
Ronkonkoma is a hamlet and census-designated place (CDP) on Long Island in the Town of Islip, New York, United States. Explore Ronkonkoma's surroundings by going to Splish Splash (in Calverton), Oyster Bay (Sagamore Hill National Historic Site & Planting Fields Arboretum State Historic Park) and Farmingdale (Bethpage Black & Adventureland). There's much more to do: test your team's savvy at popular escape rooms, look for all kinds of wild species at Avalon Park & Preserve, kick back and relax at Cupsogue Beach County Park, and stroll through Gilgo Beach.

For ratings, other places to visit, maps, and tourist information, go to the Ronkonkoma trip itinerary maker website .

New York City to Ronkonkoma is an approximately 1.5-hour car ride. Traveling from New York City in September, plan for little chillier nights in Ronkonkoma, with lows around 60°F. Finish your sightseeing early on the 16th (Mon) so you can travel to Ocean Beach.

Things to do in Ronkonkoma

Parks Outdoors Beaches

Side Trips

Huntington, Babylon, Farmingdale, Oyster Bay, Stony Brook
Highlights from your plan
Old Westbury Gardens ©
Old Westbury Gardens
Cupsogue Beach County Park ©
Cupsogue Beach County Park
Sagamore Hill National Historic Site ©

10
nights
Ocean Beach, Fire Island

Ocean Beach ©
Ocean Beach is a village in the southern part of the Town of Islip, on Fire Island, within Suffolk County, New York, United States.The Incorporated Village of Ocean Beach is a popular tourist destination, due to its beachfront location accompanied by a commercial district featuring nightlife, hotels, bayfront restaurants and a variety of stores. When in Ocean Beach, make a side trip to see Oak Beach in Oak Beach, approximately 32 minutes away. Next up on the itinerary: stroll through Ocean Beach, enjoy the sea views from Fire Island Lighthouse, delve into the lush surroundings at The Sunken Forest, and admire the majestic nature at Robert Moses State Park.

To see other places to visit, where to stay, maps, and more tourist information, go to the Ocean Beach trip planner .

You can drive from Ronkonkoma to Ocean Beach in an hour. In September, plan for daily highs up to 77°F, and evening lows to 60°F. You will leave for Montauk on the 26th (Thu).

Things to do in Ocean Beach

Parks Beaches Outdoors

Side Trips

Fire Island, Oak Beach, Kismet Beach
Highlights from your plan
Robert Moses State Park ©
Robert Moses State Park
Sailors Haven Visitor Center ©
Sailors Haven Visitor Center
Fire Island Lighthouse ©
Fire Island Lighthouse

11
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. You'll find plenty of places to visit near Montauk: East Hampton (Home Sweet Home Museum, Round Swamp Farm, & more), Bridgehampton (Channing Daughters Winery, Fairview Farm, & more) and Sag Harbor (Foster Memorial Beach, Sag Harbor Marine Park, & more). There's lots more to do: visit a coastal fixture at Montauk Point Lighthouse, pause for some serene contemplation at St. Therese of Lisieux Catholic Church, kick back and relax at Amsterdam Beach Preserve, and cast your line with a fishing tour.

To find where to stay, other places to visit, and more tourist information, refer to the Montauk online trip itinerary maker .

You can drive from Ocean Beach to Montauk in 2.5 hours. Expect a daytime high around 74°F in September, and nighttime lows around 62°F. Finish your sightseeing early on the 7th (Mon) to allow enough time to drive to Greenport.

Things to do in Montauk

Parks Outdoors Beaches

Side Trips

East Hampton, Bridgehampton, Sag Harbor, Parrish Art Museum, Wolffer Estate Vineyard
Highlights from your plan
Montauk Point Lighthouse ©
Montauk Point Lighthouse
Fishing Charters & Tours
Hither Hills State Park ©
Hither Hills State Park

12
nights
Greenport

Greenport ©
Nestled on the north fork of Long Island within a pastoral landscape of farms and vineyards, Greenport is a historic village best known for its waterfront walkway with a 36-horse vintage carousel as its centerpiece.
Explore the numerous day-trip ideas around Greenport: Riverhead (Long Island Aquarium, Tanger Outlets, & more), Mattituck (Harbes Family Farm & Macari Vineyards) and Aquebogue (North Fork Chocolate Company, Woodside Orchards, & more). And it doesn't end there: find something for the whole family at Antique Carousel, enjoy the sand and surf at Ponquogue Beach, identify plant and animal life at Mashomack Preserve, and learn about winemaking at Kontokosta Winery.

For traveler tips, where to stay, more things to do, and tourist information, read our Greenport attractions tool .

Traveling by car from Montauk to Greenport takes 2 hours. In October, daytime highs in Greenport are 64°F, while nighttime lows are 52°F. On the 19th (Sat), wrap the sightseeing up by early afternoon so you can travel back home.

Things to do in Greenport

Wineries Parks Outdoors

Side Trips

Riverhead, Cutchogue, Southold, Southampton, Peconic
Highlights from your plan
Sannino Bella Vita Vineyard ©
Sannino Bella Vita Vineyard
Antique Carousel ©
Antique Carousel
Kontokosta Winery ©
Kontokosta Winery

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