53 days in Long Island Itinerary

53 days in Long Island Itinerary

Created using Inspirock Long Island itinerary planner

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Make it your trip
Drive
1
Fire Island
— 9 nights
Drive
2
Greenport
— 11 nights
Drive
3
Shelter Island
— 10 nights
Drive
4
Montauk
— 11 nights
Drive
5
Huntington
— 11 nights
Drive

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Fire Island

— 9 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: TWA Flight 800 International Memorial (in Shirley), Bridgehampton (Mecox Beach & Fairview Farm) and Long Beach (Lido West Beach & Long Beach). Next up on the itinerary: immerse yourself in nature at Robert Moses State Park, get engrossed in the history at The Thomas Halsey Homestead, enjoy the sea views from Fire Island Lighthouse, and enjoy the sand and surf at Shinnecock East County Park.

Plan trip to Fire Island with our itinerary maker to find out where to go and what to do.

Philadelphia to Fire Island is an approximately 3.5-hour car ride. You can also drive. In July in Fire Island, expect temperatures between 84°F during the day and 69°F at night. Wrap up your sightseeing on the 9th (Tue) early enough to drive to Greenport.

Things to do in Fire Island

Parks · Outdoors · Beaches · Nature

Side Trips

Greenport

— 11 nights
Nestled on the north fork of Long Island within a pastoral landscape of farms and vineyards, Greenport is a historic village best known for its waterfront walkway with a 36-horse vintage carousel as its centerpiece.
Venture out of the city with trips to Calverton (Peconic River Herb Farm & Splish Splash), Cupsogue Beach County Park (in Westhampton Beach) and Riverhead (Riverhead Raceway, Long Island Aquarium, &more). And it doesn't end there: head outdoors with Outdoor Activities, find something for the whole family at Antique Carousel, examine the collection at East End Seaport Maritime Museum, and learn about winemaking at Sannino Bella Vita Vineyard.

To find photos, other places to visit, where to stay, and more tourist information, you can read our Greenport holiday planning site.

You can drive from Fire Island to Greenport in 2 hours. When traveling from Fire Island in August, plan for a bit cooler days and about the same nights in Greenport: temperatures range from 77°F by day to 64°F at night. Cap off your sightseeing on the 20th (Sat) early enough to go by car to Shelter Island.

Things to do in Greenport

Wineries · Theme Parks · Outdoors · Parks

Side Trips

Shelter Island

— 10 nights
Venture out of the city with trips to Bridgehampton (Children's Museum of The East End, South Fork Natural History Museum, &more) and Sag Harbor (Custom House Museum, Sag Harbor Marine Park, &more).

To find ratings, other places to visit, traveler tips, and tourist information, go to the Shelter Island trip itinerary maker site.

You can drive from Greenport to Shelter Island in an hour. In August, plan for daily highs up to 77°F, and evening lows to 64°F. On the 30th (Tue), you'll travel to Montauk.

Things to do in Shelter Island

Parks · Museums · Outdoors · Wildlife

Side Trips

Montauk

— 11 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. Venture out of the city with trips to East Hampton (LongHouse Reserve, Cedar Point County Park, &more), Channing Daughters Winery (in Bridgehampton) and Sag Harbor (First Presbyterian/Old Whaler's Church & Foster Memorial Beach). There's much more to do: cast your line with a fishing tour, immerse yourself in nature at Shadmoor State Park, stroll through Ditch Plains, and enjoy the sand and surf at Gin Beach.

For reviews, more things to do, other places to visit, and tourist information, read Montauk road trip planner.

You can drive from Shelter Island to Montauk in 1.5 hours. In August in Montauk, expect temperatures between 79°F during the day and 66°F at night. Finish up your sightseeing early on the 10th (Sat) so you can travel to Huntington.

Things to do in Montauk

Parks · Outdoors · Beaches · Nature

Side Trips

Huntington

— 11 nights
The Town of Huntington is one of ten towns in Suffolk County, New York, United States. Change things up with these side-trips from Huntington: Gilgo Beach (in Babylon), Tobay Beach (in Massapequa) and Corey Beach (in Blue Point). There's lots more to do: admire the majestic nature at Caumsett State Park, step off the mainland to explore Fire Island National Seashore, tour the pleasant surroundings at Jones Beach State Park, and admire the natural beauty at Old Westbury Gardens.

For ratings, maps, other places to visit, and more tourist information, you can read our Huntington trip app.

Traveling by car from Montauk to Huntington takes 2 hours. Expect a daytime high around 77°F in September, and nighttime lows around 61°F. Finish your sightseeing early on the 21st (Wed) to allow enough time to travel back home.

Things to do in Huntington

Parks · Outdoors · Museums · Beaches

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.