38 days in Long Island Itinerary

38 days in Long Island Itinerary

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Route & dates

38 days in Long Island Itinerary

Istanbul
Fly:  15​h 30​min
Old Westbury
— 7 nights
Drive:  1​h 15​min
Calverton
— 10 nights
Drive:  1​h 15​min
Montauk
— 12 nights
Drive:  3​h 45​min
Fire Island
— 7 nights
Fly:  16​h
Istanbul

7
days
Old Westbury

Old Westbury ©
Old Westbury is a village in Nassau County, in the U.S. Your cultural itinerary includes sights like Sands Point Preserve and Oheka Castle. Visit Jones Beach State Park and Tobay Beach for some beach relaxation. Explore the numerous day-trip ideas around Old Westbury: Bayard Cutting Arboretum (in Great River), Vanderbilt Museum and Planetarium (in Centerport) and Tanger Outlet Deer Park (in Deer Park). There's still lots to do: enjoy the sand and surf at Long Beach, have fun and explore at Long Island Children's Museum, buy something for everyone on your list at Roosevelt Field, and admire the natural beauty at Planting Fields Arboretum State Historic Park.

For where to stay, traveler tips, reviews, and other tourist information, read our Old Westbury day trip planning tool

Istanbul, Turkey to Old Westbury is an approximately 15.5-hour flight. Due to the time zone difference, you'll gain 7 hours traveling from Istanbul to Old Westbury. Traveling from Istanbul in November, expect Old Westbury to be slightly colder, temps between 13°C and 4°C. Finish your sightseeing early on the 15th (Wed) so you can travel to Calverton.

Things to do in Old Westbury

Parks Outdoors Museums

Side Trips

Garden City, Oyster Bay, Huntington, Bayard Cutting Arboretum, Tanger Outlet Deer Park
Highlights from your plan
Jones Beach State Park ©
Jones Beach State Park
Tobay Beach ©
Tobay Beach
Sands Point Preserve
Sands Point Preserve

10
days
Calverton

Calverton
Calverton is a hamlet and census-designated place (CDP) in Suffolk County, New York, United States. Satisfy your inner culture vulture at Sannino Bella Vita Vineyard and Jason's Vineyard. Relax by the water at Fire Island National Seashore and Cupsogue Beach County Park. You'll find plenty of places to visit near Calverton: Southold (The Old Field Vineyards, Croteaux Vineyards, & more), Cooper's Beach (in Southampton) and Hampton Bays (Ponquogue Beach & Meschutt Beach). And it doesn't end there: steep yourself in history at William Floyd Estate, do a tasting at Paumanok Vineyards, meet the residents at Long Island Aquarium, and cool off at Splish Splash Water Park.

To see more things to do, photos, where to stay, and tourist information, go to the Calverton day trip planner

Traveling by car from Old Westbury to Calverton takes an hour. In November, plan for daily highs up to 14°C, and evening lows to 3°C. Wrap up your sightseeing on the 25th (Sat) early enough to travel to Montauk.

Things to do in Calverton

Wineries Parks Beaches

Side Trips

Peconic, Southold, Riverhead, Jamesport, Hampton Bays
Highlights from your plan
Sannino Bella Vita Vineyard
Sannino Bella Vita Vineyard
Ponquogue Beach ©
Ponquogue Beach
Fire Island National Seashore
Fire Island National Seashore

12
days
Montauk

Montauk
Montauk is a census-designated place (CDP) that roughly corresponds to 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. Your cultural itinerary includes sights like Wölffer Estate Vineyard and Kontokosta Winery. Visit Orient Beach State Park and Ditch Plains for some beach relaxation. Get out of town with these interesting Montauk side-trips: Bridgehampton (South Fork Natural History Museum, Children's Museum of the East End, & more), Mashomack Preserve (in Shelter Island) and Sag Harbor Whaling and Historical Museum (in Sag Harbor). Next up on the itinerary: play a few rounds at Montauk Downs State Park Golf Course, look for all kinds of wild species at Elizabeth A. Morton National Wildlife Refuge, admire the majestic nature at Hither Hills State Park, and choose your vessel at Sailing Montauk's Catamaran Mon Tiki.

For ratings, maps, where to stay, and tourist information, use the Montauk driving holiday planning app

Getting from Calverton to Montauk by car takes about 1.5 hours. November in Montauk sees daily highs of 13°C and lows of 6°C at night. On the 7th (Thu), wrap the sightseeing up by early afternoon so you can travel to Fire Island.

Things to do in Montauk

Parks Outdoors Beaches

Side Trips

Bridgehampton, East Hampton, Sag Harbor Whaling and Historical Museum, Orient Beach State Park, Wölffer Estate Vineyard
Highlights from your plan
Ditch Plains
Ditch Plains
Orient Beach State Park
Orient Beach State Park
Montauk Point Lighthouse ©
Montauk Point Lighthouse

7
days
Fire Island

Fire Island
Fire Island is the large center island of the outer barrier islands parallel to the south shore of Long Island, New York. Fire Island is known for nature, historic sites, and beaches. Your plan includes some of its best attractions: tour the pleasant surroundings at Sailors Haven Visitor Center, take a peaceful walk through The Sunken Forest, visit a coastal fixture at Fire Island Lighthouse, and kick back and relax at Smith Point County Park.

To see traveler tips, other places to visit, photos, and tourist information, use the Fire Island tour itinerary planner

Traveling by car from Montauk to Fire Island takes 2.5 hours. In December, daily temperatures in Fire Island can reach 11°C, while at night they dip to 1°C. You'll set off for home on the 14th (Thu).

Things to do in Fire Island

Parks Beaches Outdoors
Highlights from your plan
Sailors Haven Visitor Center
Sailors Haven Visitor Center
Fire Island Lighthouse ©
Fire Island Lighthouse

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