60 days in Long Island Itinerary

Created using Inspirock Long Island travel planner
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Make it your trip
Drive
1
Garden City
— 14 nights
Drive
2
Montauk
— 14 nights
Drive
3
Cutchogue
— 16 nights
Drive
4
Fire Island
— 15 nights
Drive

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Garden City — 14 nights

Garden City is an incorporated village in the town of Hempstead, in central Nassau County, New York, in the United States. Get out of town with these interesting Garden City side-trips: Babylon (Argyle Park & Captree State Park), Our Lady of Grace Roman Catholic Church (in West Babylon) and Long Island Photo Gallery (in Islip). Pack the 20th (Tue) with family-friendly diversions at Adventureland. The adventure continues: see the interesting displays at Cradle of Aviation Museum, browse the exhibits of Sagamore Hill National Historic Site, browse the different shops at Roosevelt Field, and take in nature's colorful creations at Planting Fields Arboretum State Historic Park.

To see photos, where to stay, maps, and tourist information, read Garden City online travel planner.

Philadelphia to Garden City is an approximately 2.5-hour car ride. You can also drive. While traveling from Philadelphia, expect slightly colder days and about the same nights in Garden City, ranging from highs of 59°F to lows of 43°F. Finish your sightseeing early on the 28th (Wed) so you can drive to Montauk.
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Parks · Museums · Wildlife · Historic Sites
Side Trips

Montauk — 14 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. Change things up with these side-trips from Montauk: Bridgehampton (South Fork Natural History Museum, Channing Daughters Winery, &more), East Hampton (Home Sweet Home Museum, LongHouse Reserve, &more) and Sagaponack (Wolffer Estate Vineyard & Madoo Conservancy). There's still lots to do: enjoy the sea views from Montauk Point Lighthouse, walk around Navy Road Park, see what you can catch with a fishing tour, and take an in-depth tour of Second House Museum.

To see other places to visit, ratings, photos, and tourist information, read Montauk vacation builder website.

Use the Route module to find suitable travel options from Garden City to Montauk. April in Montauk sees daily highs of 55°F and lows of 41°F at night. Wrap up your sightseeing on the 12th (Wed) early enough to drive to Cutchogue.
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Parks · Outdoors · Museums · Beaches
Side Trips

Cutchogue — 16 nights

Cutchogue is a hamlet and census-designated place (CDP) in Suffolk County, New York, United States. You'll find plenty of places to visit near Cutchogue: Calverton (Splish Splash & Calverton National Cemetery), Tanger Outlets Riverhead (in Riverhead) and Shelter Island (Shelter Island Historical Society & Mashomack Preserve). And it doesn't end there: awaken your taste buds at Sannino Bella Vita Vineyard, do a tasting at Bedell Cellars, get up close and personal with brilliant marine life at Long Island Aquarium, and shop like a local with Alex Ferrone Gallery.

To see more things to do, traveler tips, other places to visit, and tourist information, read our Cutchogue road trip website.

Drive from Montauk to Cutchogue in 1.5 hours. In May, daytime highs in Cutchogue are 64°F, while nighttime lows are 52°F. Finish up your sightseeing early on the 28th (Fri) so you can go by car to Fire Island.
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Wineries · Parks · Wildlife · Historic Sites
Side Trips

Fire Island — 15 nights

Fire Island is the large center island of the outer barrier islands parallel to the south shore of Long Island, New York. You'll find plenty of places to visit near Fire Island: Southampton (Southampton History Museum, Cooper's Beach, &more), Hampton Bays (Ponquogue Beach, The Yoga House, &more) and Corey Beach (in Blue Point). The adventure continues: look for all kinds of wild species at Sailors Haven Visitor Center, enjoy the sand and surf at Kismet Beach, stroll through Ocean Beach, and enjoy the sea views from Fire Island Lighthouse.

To find maps, more things to do, where to stay, and tourist information, read our Fire Island sightseeing planner.

You can drive from Cutchogue to Fire Island in 2 hours. In May, plan for daily highs up to 69°F, and evening lows to 51°F. On the 12th (Sat), you're off to home.
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Parks · Outdoors · Beaches · Museums
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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