60 days in Long Island Itinerary

60 days in Long Island Itinerary

Created using Inspirock Long Island attractions planner

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Route & dates

60 days in Long Island Itinerary

Start: Newark
Drive:  1​h 30​min
1
Centerport
— 12 nights
Drive:  2​h
2
Montauk
— 11 nights
Drive:  1​h 15​min
3
Shelter Island
— 12 nights
Drive:  3​h 30​min
4
Ocean Beach, Fire Island
— 12 nights
Drive:  3​h 15​min
5
Southold
— 12 nights
Drive:  2​h 30​min
End: Newark

12
nights
Centerport

Centerport ©
Centerport is a hamlet and census-designated place (CDP) in Suffolk County, New York, United States, on the notably affluent North Shore of Long Island. You'll explore and learn at Sagamore Hill National Historic Site and American Airpower Museum. Deepen your sense of the past at sights like Sands Point Preserve and St. James General Store. Change things up with these side-trips from Centerport: Holtsville Ecology Site (in Holtsville), Nassau County Museum of Art (in Roslyn) and Garden City (Long Island Children's Museum & Cradle of Aviation Museum). There's still lots to do: look for all kinds of wild species at Bayard Cutting Arboretum, explore the activities along Wertheim National Wildlife Refuge, take a peaceful walk through Cold Spring Harbor State Park, and examine the collection at Vanderbilt Museum and Planetarium.

To see reviews, where to stay, ratings, and other tourist information, refer to the Centerport trip itinerary maker app .

Newark to Centerport is an approximately 1.5-hour car ride. When traveling from Newark in June, plan for a bit cooler days and about the same nights in Centerport: temperatures range from 77°F by day to 62°F at night. Finish up your sightseeing early on the 13th (Thu) so you can travel to Montauk.

Things to do in Centerport

Parks Museums Outdoors

Side Trips

Huntington, Oyster Bay, Stony Brook, Glen Cove, Garden City
Highlights from your plan
Sands Point Preserve ©
Sands Point Preserve
Sagamore Hill National Historic Site ©
Bayard Cutting Arboretum ©
Bayard Cutting Arboretum

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. Get outdoors at Fishing Charters & Tours and Montauk Point State Park. Get a sense of the local culture at Montauk Point Lighthouse and Main Beach. You'll find plenty of places to visit near Montauk: East Hampton (Home Sweet Home Museum, Guild Hall, & more) and Race Rock Lighthouse (in Fishers Island). There's still lots to do: enjoy the sand and surf at Amsterdam Beach Preserve, tour the pleasant surroundings at Ditch Plains, steep yourself in history at Pollock-Krasner House and Study Center, and explore and take pictures at Camp Hero State Park.

To see other places to visit, traveler tips, photos, and other tourist information, go to the Montauk trip planner .

Drive from Centerport to Montauk in 2 hours. Expect a daytime high around 74°F in June, and nighttime lows around 60°F. Finish your sightseeing early on the 24th (Mon) so you can drive to Shelter Island.

Things to do in Montauk

Parks Outdoors Beaches

Side Trips

East Hampton, Race Rock Lighthouse
Highlights from your plan
Montauk Point Lighthouse ©
Montauk Point Lighthouse
Fishing Charters & Tours
Guild Hall ©
Guild Hall

12
nights
Shelter Island

Shelter Island ©
Shelter Island is a hamlet and census-designated place (CDP) within the Town of Shelter Island in Suffolk County, New York, United States. Get in touch with nature at Mashomack Preserve and Sylvester Manor Educational Farm. The adventure continues: steep yourself in history at Shelter Island Historical Society and indulge your thirst for a good beer at Shelter Island Craft Brewery.

To find reviews, other places to visit, traveler tips, and more tourist information, read Shelter Island tour site .

Traveling by car from Montauk to Shelter Island takes 1.5 hours. In June in Shelter Island, expect temperatures between 73°F during the day and 60°F at night. You'll set off for Ocean Beach on the 6th (Sat).

Things to do in Shelter Island

Parks Wildlife Historic Sites
Highlights from your plan
Mashomack Preserve ©
Mashomack Preserve
Shelter Island Historical Society ©
Shelter Island Historical Society
Sylvester Manor Educational Farm ©
Sylvester Manor Educational Farm

12
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. Get outdoors at Sailors Haven Visitor Center and Kismet Beach. And it doesn't end there: walk around Robert Moses State Park, stroll through Ocean Beach, delve into the lush surroundings at The Sunken Forest, and enjoy the sea views from Fire Island Lighthouse.

To find reviews, maps, where to stay, and tourist information, read Ocean Beach trip itinerary builder .

You can drive from Shelter Island to Ocean Beach in 2.5 hours. Expect a daytime high around 84°F in July, and nighttime lows around 69°F. On the 18th (Thu), you're off toSouthold.

Things to do in Ocean Beach

Parks Beaches Outdoors

Side Trips

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

12
nights
Southold

Southold ©
The Town of Southold is one of ten towns in Suffolk County, New York, United States. You'll explore and learn at Oysterponds Historical Society and Parrish Art Museum. Your cultural itinerary includes sights like William Floyd Estate and The Thomas Halsey Homestead. Venture out of the city with trips to Baiting Hollow Hummingbird Sanctuary (in Baiting Hollow), Calverton (Splish Splash & Calverton National Cemetery) and Paumanok Vineyards (in Aquebogue). There's much more to do: identify plant and animal life at Quogue Wildlife Refuge, do a tasting at Sparkling Pointe, take an in-depth tour of Southold Historical Society, and kick back and relax at Cooper's Beach.

For reviews, where to stay, photos, and tourist information, read our Southold trip planner .

Traveling by car from Ocean Beach to Southold takes 2 hours. Traveling from Ocean Beach in July, you will find days in Southold are slightly colder (79°F), and nights are about the same (67°F). Wrap up your sightseeing on the 30th (Tue) early enough to travel back home.

Things to do in Southold

Parks Wineries Beaches

Side Trips

Cutchogue, Riverhead, Peconic, Sag Harbor, Southampton
Highlights from your plan
Cupsogue Beach County Park ©
Cupsogue Beach County Park
Quogue Wildlife Refuge ©
Quogue Wildlife Refuge
Oysterponds Historical Society ©
Oysterponds Historical Society

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