60 days in Long Island Itinerary

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: Long Island Photo Gallery (in Islip), Our Lady of Grace Roman Catholic Church (in West Babylon) and Babylon (Argyle Park & Captree State Park). Pack the 20th (Tue) with family-friendly diversions at Adventureland. There's much more to do: examine the collection at Cradle of Aviation Museum, identify plant and animal life at Norman J. Levy Park & Preserve, contemplate the long history of Cathedral of the Incarnation, and browse the exhibits of Planting Fields Arboretum State Historic Park.

Plan a Garden City trip in moments using our itinerary builder.

Philadelphia to Garden City is an approximately 2.5-hour car ride. Traveling from Philadelphia in April, expect nights in Garden City to be about the same, around 43°F, while days are little chillier, around 59°F. Finish your sightseeing early on the 28th (Wed) so you can travel to Montauk.

Things to do in Garden City

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. You'll find plenty of places to visit near Montauk: East Hampton (Home Sweet Home Museum, LongHouse Reserve, &more), Sagaponack (Wolffer Estate Vineyard & Madoo Conservancy) and Bridgehampton (South Fork Natural History Museum, Channing Daughters Winery, &more). The adventure continues: visit a coastal fixture at Montauk Point Lighthouse, go for a stroll along the water at Star Island Yacht Club and Marina, walk around Navy Road Park, and immerse yourself in nature at Shadmoor State Park.

Find out how to plan Montauk trip without stress by asking Inspirock to help create an itinerary.

You can drive from Garden City to Montauk in 2 hours. In April in Montauk, expect temperatures between 55°F during the day and 41°F at night. Cap off your sightseeing on the 12th (Wed) early enough to go by car to Cutchogue.

Things to do in Montauk

Parks · Outdoors · Museums · Nature

Side Trips

Cutchogue

— 16 nights
Cutchogue is a hamlet and census-designated place (CDP) in Suffolk County, New York, United States. Get out of town with these interesting Cutchogue side-trips: Tanger Outlets Riverhead (in Riverhead), Shelter Island (Shelter Island Historical Society & Mashomack Preserve) and Calverton (Splish Splash & Calverton National Cemetery). And it doesn't end there: take in the exciting artwork at Alex Ferrone Gallery, do a tasting at Sannino Bella Vita Vineyard, indulge your senses at some of the top wineries in the area, and admire nature's wide array of creatures at Long Island Aquarium.

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.

Things to do in Cutchogue

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: Corey Beach (in Blue Point), Southampton (Southampton History Museum, Cooper's Beach, &more) and Hampton Bays (Ponquogue Beach, House of Wellness, &more). 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.

Things to do in Fire Island

Parks · Beaches · Outdoors · Museums

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.