34 days in Long Island Itinerary

34 days in Long Island Itinerary

Created using Inspirock Long Island trip planner

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Route & dates

34 days in Long Island Itinerary

Start: Orlando
Fly + Drive:  7​h 45​min
1
Ocean Beach, Fire Island
— 9 nights
Drive:  2​h 15​min
2
Montauk
— 9 nights
Drive:  1​h 30​min
3
Southold
— 8 nights
Drive:  1​h 30​min
4
Huntington
— 7 nights
Drive + Fly:  5​h 30​min
End: Orlando

9
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. You'll find plenty of places to visit near Ocean Beach: Fire Island National Seashore (in Patchogue), Hicks Nurseries (in Westbury) and Massapequa (Massapequa Preserve & Marjorie R. Post Community Park). The adventure continues: test your problem-solving skills at popular escape rooms, look for all kinds of wild species at Holtsville Ecology Site, walk around Norman J. Levy Park & Preserve, and enjoy the sea views from Fire Island Lighthouse.

To see traveler tips, other places to visit, photos, and more tourist information, refer to the Ocean Beach trip planner .

Orlando to Ocean Beach is an approximately 8-hour combination of flight and car. Expect a bit cooler temperatures when traveling from Orlando in October; daily highs in Ocean Beach reach 67°F and lows reach 50°F. Wrap up your sightseeing on the 26th (Sat) to allow time to travel to Montauk.

Things to do in Ocean Beach

Parks Nature Outdoors

Side Trips

Farmingdale, Fire Island, Massapequa, Old Bethpage, Long Beach
Find places to stay Oct 17 — 26:
Highlights from your plan
Fire Island National Seashore ©
Fire Island National Seashore
Room Escape Games
Bayard Cutting Arboretum ©
Bayard Cutting Arboretum

9
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. Venture out of the city with trips to East Hampton (Guild Hall, Home Sweet Home Museum, & more), Sagaponack (Wolffer Estate Vineyard & Madoo Conservancy) and Bridgehampton (South Fork Natural History Museum, Children's Museum of The East End, & more). There's still lots to do: visit a coastal fixture at Montauk Point Lighthouse, admire the majestic nature at Hither Hills State Park, sample the tasty concoctions at Montauk Brewing Company, and don't miss a visit to Gosman's Restaurant.

To find other places to visit, reviews, maps, and more tourist information, use the Montauk trip itinerary app .

Getting from Ocean Beach to Montauk by car takes about 2.5 hours. In October in Montauk, expect temperatures between 65°F during the day and 53°F at night. Cap off your sightseeing on the 4th (Mon) early enough to go by car to Southold.

Things to do in Montauk

Parks Outdoors Museums

Side Trips

East Hampton, Bridgehampton, Sag Harbor, Sagaponack
Find places to stay Oct 26 — Nov 4:
Highlights from your plan
Montauk Point Lighthouse ©
Montauk Point Lighthouse
Fishing Charters & Tours
Montauk Point State Park ©
Montauk Point State Park

8
nights
Southold

Southold ©
The Town of Southold is one of ten towns in Suffolk County, New York, United States. Venture out of the city with trips to Quogue Wildlife Refuge (in Quogue), Riverhead (Tanger Outlets & Long Island Aquarium) and Splish Splash (in Calverton). There's lots more to do: see the sky in a new way at Custer Institute & Observatory, find something for the whole family at Antique Carousel, tour the pleasant surroundings at Cooper's Beach, and experience rural life at The East End Mushroom Company.

To find photos, ratings, more things to do, and other tourist information, you can read our Southold online travel planner .

Getting from Montauk to Southold by car takes about 1.5 hours. In November, daily temperatures in Southold can reach 51°F, while at night they dip to 40°F. Wrap up your sightseeing on the 12th (Tue) to allow time to travel to Huntington.

Things to do in Southold

Parks Wildlife Theme Parks

Side Trips

Cutchogue, Greenport, Riverhead, Mattituck, Southampton
Find places to stay Nov 4 — 12:
Highlights from your plan
Long Island Aquarium ©
Long Island Aquarium
Sparkling Pointe Vineyards & Winery ©
Custer Institute & Observatory ©
Custer Institute & Observatory

7
nights
Huntington

Huntington ©
The Town of Huntington is one of ten towns in Suffolk County, New York, United States. Step out of Huntington with an excursion to Morgan Memorial Park in Glen Cove--about 30 minutes away. There's lots more to do: walk around Caumsett State Park, gain insight at Cold Spring Harbor Laboratory, browse the exhibits of Sagamore Hill National Historic Site, and browse the fresh offerings at Kerber's farm.

For traveler tips, reviews, ratings, and other tourist information, read our Huntington trip planner .

Traveling by car from Southold to Huntington takes 1.5 hours. Expect a daytime high around 54°F in November, and nighttime lows around 39°F. Finish up your sightseeing early on the 19th (Tue) so you can travel back home.

Things to do in Huntington

Parks Museums Wildlife

Side Trips

Oyster Bay, Glen Cove, Makinajian Poultry Farm, Vanderbilt Museum and Planetarium, Northport Village Park
Find places to stay Nov 12 — 19:
Highlights from your plan
Caumsett State Park ©
Caumsett State Park
Book Revue ©
Book Revue
Cold Spring Harbor State Park ©
Cold Spring Harbor State Park

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