43 days in Long Island & Elgin Itinerary

43 days in Long Island & Elgin Itinerary

Created using Inspirock United States travel planner
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Make it your trip
Fly to John F Kennedy International Airport, Drive to Huntington
1
Huntington
— 4 nights
Drive
2
Fire Island
— 3 nights
Drive
3
Cutchogue
— 5 nights
Drive
4
Montauk
— 7 nights
+2
Drive to John F Kennedy International Airport, Fly to Chicago O'Hare International Airport, Drive to Elgin
5
Elgin
— 23 nights
Drive to Chicago O'Hare International Airport, Fly to Los Angeles

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Huntington — 4 nights

The Town of Huntington is one of ten towns in Suffolk County, New York, United States. Shop till you drop at St. James General Store and Tanger Outlets Deer Park. Museum-lovers will appreciate Long Island Maritime Museum and Sagamore Hill National Historic Site. Venture out of the city with trips to Ho-hum Beach (in Bellport), Sagtikos Manor (in Bay Shore) and Fire Island National Seashore (in Patchogue). There's much more to do: stroll through Jones Beach State Park, steep yourself in history at Walt Whitman Birthplace, and identify plant and animal life at Sands Point Preserve.

For traveler tips, more things to do, photos, and other tourist information, read our Huntington route planning website.

Los Angeles to Huntington is an approximately 9-hour combination of flight and car. You can also drive. Traveling from Los Angeles to Huntington, you'll lose 3 hours due to the time zone difference. Traveling from Los Angeles in September, expect Huntington to be little chillier, temps between 77°F and 61°F. Finish your sightseeing early on the 24th (Fri) so you can drive to Fire Island.
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Parks · Historic Sites · Outdoors · Beaches
Side Trips

Fire Island — 3 nights

Fire Island is the large center island of the outer barrier islands parallel to the south shore of Long Island, New York. Visiting Cooper's Beach and Kismet Beach will get you outdoors. You'll enjoy a bit of beach vacationing at Long Beach and Ponquogue Beach. The adventure continues: visit a coastal fixture at Fire Island Lighthouse and tour the pleasant surroundings at Ocean Beach.

To plan Fire Island vacation without wasting time, ask Inspirock to design an itinerary.

Drive from Huntington to Fire Island in 1.5 hours. In September, daily temperatures in Fire Island can reach 77°F, while at night they dip to 60°F. Wrap up your sightseeing on the 27th (Mon) to allow time to drive to Cutchogue.
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Outdoors · Parks · Beaches · Historic Sites
Side Trips

Cutchogue — 5 nights

Cutchogue is a hamlet and census-designated place (CDP) in Suffolk County, New York, United States. Southold Historical Museum and Alex Ferrone Gallery will appeal to museum buffs. Relax by the water at Orient Beach State Park and Smith Point County Park. Explore the numerous day-trip ideas around Cutchogue: Shelter Island Historical Society (in Shelter Island), Tanger Outlets Riverhead (in Riverhead) and Cupsogue Beach County Park (in Westhampton Beach). There's still lots to do: savor the flavors at Food & Drink, take a tour by water with Boat Tours & Water Sports, and do a tasting at Sparkling Pointe Vineyards & Winery.

For traveler tips and other tourist information, go to the Cutchogue trip planning website.

Getting from Fire Island to Cutchogue by car takes about 2 hours. Traveling from Fire Island in September, you will find days in Cutchogue are little chillier (72°F), and nights are about the same (59°F). Cap off your sightseeing on the 2nd (Sat) early enough to go by car to Montauk.
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Wineries · Outdoors · Shopping · Parks
Side Trips

Montauk — 7 nights

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. Head to Main Beach and Round Swamp Farmfor plenty of shopping. Your inner history buff will appreciate Montauk Point Lighthouse and Camp Hero State Park. Explore Montauk's surroundings by going to Wolffer Estate Vineyard (in Sagaponack) and Foster Memorial Beach (in Sag Harbor). There's much more to do: see majestic marine mammals with Viking Fleet, admire the majestic nature at Montauk Point State Park, enjoy the sand and surf at Gin Beach, and make a trip to Gosman's Restaurant.

To see traveler tips, ratings, other places to visit, and other tourist information, use the Montauk trip builder tool.

You can drive from Cutchogue to Montauk in 1.5 hours. In October, daytime highs in Montauk are 65°F, while nighttime lows are 53°F. Wrap up your sightseeing on the 9th (Sat) to allow time to drive to Elgin.
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Parks · Outdoors · Beaches · Nature
Side Trips

Elgin — 23 nights

Elgin is a city in Cook and Kane counties in the northern part of the U.S. state of Illinois. Visit Cantigny Park and Livingston County Courthouse for their historical value. Museum-lovers will appreciate IL Route 66 Association Hall of Fame & Museum and Illinois Railway Museum. You'll find plenty of places to visit near Elgin: Wheaton (Illinois Prairie Path & French Market), Pontiac (International Wall Dog Mural and Sign Art Museum, Livingston County War Museum, &more) and Moraine Hills State Park (in McHenry). There's much more to do: indulge your taste buds at Whiskey Acres Distilling Co., get some fabulous bargains at Chicago Premium Outlets, get to know the fascinating history of Riverwalk Lot, and tee off at Mistwood Golf Club.

For photos, maps, and tourist information, read Elgin travel planner.

Explore your travel options from Montauk to Elgin with the Route module. The time zone difference when traveling from Montauk to Elgin is minus 1 hour. Traveling from Montauk in October, you can expect nighttime temperatures to be a bit cooler in Elgin, with lows of 44°F. Finish up your sightseeing early on the 1st (Mon) so you can go by car back home.
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Museums · Parks · Outdoors · Shopping
Side Trips

Long Island travel guide

4.4
Wineries & Vineyards · Beaches · Lighthouses
Stretching northeast from New York Harbor to the Atlantic Ocean, Long Island is the largest island in the continental U.S. It technically includes the New York City boroughs of Brooklyn and Queens, but generally refers to the suburban counties of Nassau and Suffolk exclusively. Known for its cookie-cutter suburban neighborhoods, the island is also home to a wealth of intriguing places to visit, including beaches, scenic countryside, wineries, and numerous historical sites. In the summer months, wealthy New Yorkers flock here to relax in their exclusive Hamptons properties.
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