30 days in Long Island Itinerary

Created using Inspirock Long Island trip itinerary planner
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Make it your trip
Fly to John F Kennedy International Airport, Drive to Garden City
1
Garden City
— 6 nights
Drive
2
Fire Island
— 6 nights
Drive
3
Greenport
— 7 nights
Drive
4
Montauk
— 9 nights
Drive to John F Kennedy International Airport, Fly to New Delhi

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Garden City — 6 nights

Garden City is an incorporated village in the town of Hempstead, in central Nassau County, New York, in the United States. Explore the numerous day-trip ideas around Garden City: Smith Haven Mall (in Lake Grove), Avalon Park & Preserve (in Stony Brook) and Room Escape Games (in Ronkonkoma). There's much more to do: examine the collection at Cradle of Aviation Museum, steep yourself in history at Old Bethpage Village Restoration, look for all kinds of wild species at Bayard Cutting Arboretum, and walk around Planting Fields Arboretum State Historic Park.

To see photos, ratings, and tourist information, use the Garden City journey planner.

New Delhi, India to Garden City is an approximately 22.5-hour combination of flight and car. The time zone changes from India Standard Time to Eastern Standard Time, which is usually a -10.5 hour difference. In January, Garden City is colder than New Delhi - with highs of 5°C and lows of -3°C. Wrap up your sightseeing on the 7th (Sat) early enough to drive to Fire Island.
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Parks · Museums · Historic Sites · Wildlife
Side Trips

Fire Island — 6 nights

Fire Island is the large center island of the outer barrier islands parallel to the south shore of Long Island, New York. Explore Fire Island's surroundings by going to Southampton (Agawam Park, Southampton Arts Center, &more), Shirley (The Museum Manor of St. George & TWA Flight 800 International Memorial) and Holtsville Ecology Site (in Holtsville). There's much more to do: take in the waterfront activity at Sailors Haven Visitor Center, take in the architecture and atmosphere at Church of St. Rosalie, sample the tasty concoctions at Moustache Brewing Co, and enjoy the sea views from Fire Island Lighthouse.

To find photos, traveler tips, maps, and tourist information, use the Fire Island vacation planner.

Drive from Garden City to Fire Island in 1.5 hours. In January, plan for daily highs up to 4°C, and evening lows to -5°C. Finish your sightseeing early on the 13th (Fri) so you can drive to Greenport.
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Parks · Museums · Historic Sites · Outdoors
Side Trips

Greenport — 7 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.
Explore Greenport's surroundings by going to Massage Envy (in Rocky Point), Shrine of Our Lady of the Island (in Manorville) and Riverhead (Tanger Outlets Riverhead & Long Island Aquarium). Next up on the itinerary: get a new perspective on things with Boat Tours & Water Sports, examine the collection at East End Seaport Maritime Museum, indulge your taste buds at Food & Drink, and get a taste of the local shopping with Alex Ferrone Gallery.

For photos, where to stay, and tourist information, read our Greenport road trip planning tool.

Traveling by car from Fire Island to Greenport takes 2.5 hours. January in Greenport sees daily highs of 3°C and lows of -3°C at night. Finish your sightseeing early on the 20th (Fri) to allow enough time to drive to Montauk.
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Wineries · Tours · Shopping · Parks
Side Trips

Montauk — 9 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 Bridgehampton (South Fork Natural History Museum & Children's Museum of The East End), Wolffer Estate Vineyard (in Sagaponack) and Sag Harbor (Sag Harbor Marine Park, Custom House Museum, &more). Next up on the itinerary: cast your line with a fishing tour, immerse yourself in nature at Camp Hero State Park, enjoy the sand and surf at Ditch Plains, and get engrossed in the history at Second House Museum.

To find more things to do, traveler tips, reviews, and more tourist information, you can read our Montauk trip planner.

You can drive from Greenport to Montauk in 2 hours. In January in Montauk, expect temperatures between 4°C during the day and -2°C at night. Wrap up your sightseeing by early afternoon on the 29th (Sun) to allow time for travel back home.
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Parks · Museums · Outdoors · Historic Sites
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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