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), Fire Island National Seashore (in Patchogue) and Sagtikos Manor (in Bay Shore). There's much more to do: stroll through Jones Beach State Park, steep yourself in history at Walt Whitman Birthplace, and explore and take pictures 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 9.5-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.

Things to do in Huntington

Parks · Historic Sites · Beaches · Outdoors

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.

Things to do in Fire Island

Beaches · Parks · Outdoors · 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 Cupsogue Beach County Park. Explore the numerous day-trip ideas around Cutchogue: Tanger Outlets Riverhead (in Riverhead), Smith Point County Park (in Shirley) and Shelter Island Historical Society (in Shelter Island). 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.

Things to do in Cutchogue

Wineries · Outdoors · Beaches · 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 Pollock-Krasner House and Study Center. Explore Montauk's surroundings by going to Wolffer Estate Vineyard (in Sagaponack) and Foster Memorial Beach (in Sag Harbor). There's lots more to do: see majestic marine mammals with Viking Fleet, admire the majestic nature at Montauk Point State Park, stroll through Camp Hero State Park, and enjoy the sand and surf at Gin Beach.

To find other places to visit, traveler tips, ratings, and tourist information, go to the Montauk road trip tool.

You can drive from Cutchogue to Montauk in 1.5 hours. In October, plan for daily highs up to 65°F, and evening lows to 53°F. Finish up your sightseeing early on the 9th (Sat) so you can travel to Elgin.

Things to do in Montauk

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: Pontiac (International Wall Dog Mural and Sign Art Museum, Livingston County War Museum, &more), Moraine Hills State Park (in McHenry) and Wheaton (First Division Museum at Cantigny, Illinois Prairie Path, &more). The adventure continues: explore and take pictures at Whiskey Acres Distilling Co., get to know the fascinating history of Riverwalk Lot, examine the collection at Volo Auto Museum, and kick back and relax at Centennial Beach.

To see reviews, where to stay, other places to visit, and other tourist information, read Elgin route planning tool.

The Route module can help you plan travel from Montauk to Elgin. Due to the time zone difference, you'll gain 1 hour traveling from Montauk to Elgin. Traveling from Montauk in October, Elgin is a bit cooler at night with lows of 44°F. Finish your sightseeing early on the 1st (Mon) so you can travel back home.

Things to do in Elgin

Museums · Parks · Outdoors · Nature

Side Trips

Long Island travel guide

4.3
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.