20 days in Long Island Itinerary

20 days in Long Island Itinerary

Created using Inspirock Long Island visit planner

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Route & dates

20 days in Long Island Itinerary

Start: San Francisco
Fly + Drive:  9​h 45​min
1
Ronkonkoma
— 5 nights
Drive:  1​h
2
Ocean Beach, Fire Island
— 3 nights
Drive:  2​h 15​min
3
Montauk
— 6 nights
Drive:  1​h 45​min
4
Greenport
— 5 nights
Drive + Fly:  10​h 30​min
End: San Francisco

5
nights
Ronkonkoma

Ronkonkoma ©
Ronkonkoma is a hamlet and census-designated place (CDP) on Long Island in the Town of Islip, New York, United States. Venture out of the city with trips to Splish Splash (in Calverton), Oyster Bay (Sagamore Hill National Historic Site & Planting Fields Arboretum State Historic Park) and Huntington (Book Revue & Kerber's farm). There's lots more to do: test your problem-solving skills at popular escape rooms, stroll through Jones Beach State Park, examine the collection at Cradle of Aviation Museum, and admire the natural beauty at Old Westbury Gardens.

To find ratings, traveler tips, reviews, and tourist information, go to the Ronkonkoma route tool .

San Francisco to Ronkonkoma is an approximately 10-hour combination of flight and car. You can also drive. Due to the time zone difference, you'll lose 3 hours traveling from San Francisco to Ronkonkoma. Expect a daytime high around 77°F in September, and nighttime lows around 60°F. Wrap up your sightseeing on the 23rd (Mon) to allow time to travel to Ocean Beach.

Things to do in Ronkonkoma

Parks Beaches Outdoors

Side Trips

Huntington, Oyster Bay, Garden City, Jones Beach State Park, Avalon Park & Preserve
Highlights from your plan
Old Westbury Gardens ©
Old Westbury Gardens
Cupsogue Beach County Park ©
Cupsogue Beach County Park
Sagamore Hill National Historic Site ©

3
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. Change things up with a short trip to Nickerson Beach Park in Lido Beach (about 50 minutes away). There's still lots to do: tour the pleasant surroundings at Ocean Beach, go for a stroll along the water at Sailors Haven Visitor Center, visit a coastal fixture at Fire Island Lighthouse, and delve into the lush surroundings at The Sunken Forest.

To see photos, traveler tips, maps, and other tourist information, read Ocean Beach itinerary builder site .

Traveling by car from Ronkonkoma to Ocean Beach takes an hour. September in Ocean Beach sees daily highs of 77°F and lows of 60°F at night. Finish your sightseeing early on the 26th (Thu) so you can travel to Montauk.

Things to do in Ocean Beach

Parks Beaches Outdoors

Side Trips

Fire Island, Nickerson Beach Park, 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

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. Change things up with these side-trips from Montauk: Wolffer Estate Vineyard (in Sagaponack), Sag Harbor (Foster Memorial Beach & First Presbyterian/Old Whaler's Church) and Guild Hall (in East Hampton). The adventure continues: enjoy the sea views from Montauk Point Lighthouse, stroll through Amsterdam Beach Preserve, kick back and relax at Kirk Park Beach, and get interesting insight from Tours.

For where to stay, other places to visit, maps, and tourist information, refer to the Montauk trip itinerary planning site .

You can drive from Ocean Beach to Montauk in 2.5 hours. In September, daily temperatures in Montauk can reach 74°F, while at night they dip to 62°F. Wrap up your sightseeing on the 2nd (Wed) early enough to drive to Greenport.

Things to do in Montauk

Parks Outdoors Beaches

Side Trips

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

5
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.
Get out of town with these interesting Greenport side-trips: Shelter Island (Shelter Island Historical Society & Mashomack Preserve) and Riverhead (Long Island Aquarium & Tanger Outlets). The adventure continues: get in on the family fun at Antique Carousel, learn about winemaking at Pindar Vineyards, enjoy the sand and surf at Cooper's Beach, and indulge your taste buds at Food & Drink.

For where to stay, ratings, other places to visit, and other tourist information, use the Greenport visit planner .

Traveling by car from Montauk to Greenport takes 2 hours. October in Greenport sees daily highs of 64°F and lows of 52°F at night. Wrap up your sightseeing on the 7th (Mon) early enough to travel back home.

Things to do in Greenport

Wineries Parks Theme Parks

Side Trips

Shelter Island, Peconic, Cutchogue, Riverhead, Sparkling Pointe Vineyards & Winery
Highlights from your plan
Sannino Bella Vita Vineyard ©
Sannino Bella Vita Vineyard
Antique Carousel ©
Antique Carousel
Long Island Aquarium ©
Long Island Aquarium

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