44 days in Long Island Itinerary

44 days in Long Island Itinerary

Created using Inspirock Long Island trip itinerary planner

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Plan created by another user.Make it yours

Route & dates

Start: Newark
Drive:  3 h
1
Montauk
— 14 nights
Drive:  1 h 30 min
2
Cutchogue
— 15 nights
Drive:  1 h 30 min
3
Farmingdale
— 14 nights
Drive:  1 h 15 min
End: Newark

14
nights
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. Second House Museum and Sag Harbor Whaling and Historical Museum will appeal to museum buffs. Deepen your sense of the past at sights like Montauk Point Lighthouse and Pollock-Krasner House and Study Center. Explore Montauk's surroundings by going to Southold (Southold Bay Oysters, The Old Field Vineyards, &more), Orient (Orient Beach State Park, Oysterponds Historical Society, &more) and Greenport (Congregation Tifereth Israel, Railroad Museum of Long Island, &more). The adventure continues: enjoy the sand and surf at Ditch Plains, play a few rounds at Montauk Downs State Park Golf Course, take a tour by water with Boat Tours & Water Sports, and sample the tasty concoctions at Montauk Brewing Company.

To see more things to do, maps, photos, and tourist information, read Montauk day trip website.

Newark to Montauk is an approximately 3-hour car ride. You can also take a train; or take a bus. Traveling from Newark in June, you will find days in Montauk are little chillier (74°F), and nights are about the same (60°F). Wrap up your sightseeing on the 28th (Fri) early enough to drive to Cutchogue.

Things to do in Montauk

Parks Outdoors Beaches

Side Trips

Southold, East Hampton, Sag Harbor, Greenport, Orient
Highlights from your plan
Fishing Charters & Tours
Orient Beach State Park ©
Orient Beach State Park
The Leiber Collection ©
The Leiber Collection

15
nights
Cutchogue

Cutchogue ©
Cutchogue is a hamlet and census-designated place (CDP) in Suffolk County, New York, United States. Step off the beaten path and head to Wine Tours & Tastings and Pugliese Vineyards. Step out of the city life by going to Elizabeth A. Morton National Wildlife Refuge and Flying Point Beach. Change things up with these side-trips from Cutchogue: Southampton (Southampton Arts Center, Agawam Park, &more), Water Mill (Hank's Pumpkintown, Parrish Art Museum, &more) and Bridgehampton (Bridge Gardens, Children's Museum of The East End, &more). There's more to do: learn about winemaking at Coffee Pot Cellars Tasting Room and take in the exciting artwork at Alex Ferrone Gallery.

For where to stay, reviews, photos, and more tourist information, refer to the Cutchogue travel route builder.

You can drive from Montauk to Cutchogue in 1.5 hours. In June, daytime highs in Cutchogue are 73°F, while nighttime lows are 60°F. Finish your sightseeing early on the 13th (Sat) so you can travel to Farmingdale.

Things to do in Cutchogue

Wineries Parks Museums

Side Trips

Southampton, Peconic, Bridgehampton, Mattituck, Jamesport
Highlights from your plan
Elizabeth A. Morton National Wildlife Refuge ©
Wine Tours & Tastings
Parrish Art Museum ©
Parrish Art Museum

14
nights
Farmingdale

Farmingdale ©
The Incorporated Village of Farmingdale is an incorporated village on Long Island within the Town of Oyster Bay in Nassau County, New York, in the United States. Get some historical perspective at Sagamore Hill National Historic Site and Queens County Farm Museum. Step off the beaten path and head to Jones Beach State Park and American Airpower Museum. Change things up with these side-trips from Farmingdale: William Floyd Estate (in Mastic Beach), Hampton Bays (Church of St. Rosalie & Meschutt Beach) and Quogue Wildlife Refuge (in Quogue). There's still lots to do: take an in-depth tour of Long Island Maritime Museum, contemplate the long history of Old Bethpage Village Restoration, look for all kinds of wild species at Wertheim National Wildlife Refuge, and learn about winemaking at Sparkling Pointe Vineyards & Winery.

To see more things to do, photos, maps, and tourist information, refer to the Farmingdale trip planner.

Drive from Cutchogue to Farmingdale in 1.5 hours. In July, plan for daily highs up to 83°F, and evening lows to 69°F. Wrap up your sightseeing on the 27th (Sat) to allow time to drive back home.

Things to do in Farmingdale

Parks Wildlife Museums

Side Trips

Garden City, Stony Brook, Southampton, Shirley, Huntington
Highlights from your plan
William Floyd Estate ©
William Floyd Estate
Sagamore Hill National Historic Site ©
Sagamore Hill National Historic Site
Bayard Cutting Arboretum ©
Bayard Cutting Arboretum

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