5 days in Long Island Itinerary

5 days in Long Island Itinerary

Created using Inspirock Long Island holiday planner

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Plan created by another user. Make it yours
Drive
1
Garden City
— 1 night
Drive
2
Riverhead
— 1 night
Drive
3
Montauk
— 2 nights
Drive

S M T W T F S
29
30
31
1
2
3
4

1
night
Garden City

Garden City is an incorporated village in the town of Hempstead, in central Nassau County, New York, in the United States. On the 29th (Sun), take in nature's colorful creations at Planting Fields Arboretum State Historic Park and then contemplate the long history of Sagamore Hill National Historic Site. On the 30th (Mon), you'll have a packed day of sightseeing: see the interesting displays at Cradle of Aviation Museum, then take in nature's colorful creations at Old Westbury Gardens, and then take an in-depth tour of American Guitar Museum.

To see maps, where to stay, and other tourist information, use the Garden City day trip website.

Smithtown to Garden City is an approximately 1-hour car ride. December in Garden City sees daily highs of 47°F and lows of 35°F at night. Wrap up your sightseeing on the 30th (Mon) early enough to travel to Riverhead.

Things to do in Garden City

Parks · Museums · Historic Sites

Side Trips

1
night
Riverhead

Riverhead is a town within Suffolk County, New York, on the north shore of Long Island. Start off your visit on the 31st (Tue): test your team's savvy at popular escape rooms and then stroll through Cooper's Beach.

For more things to do, other places to visit, and tourist information, use the Riverhead trip itinerary planner.

Traveling by car from Garden City to Riverhead takes 1.5 hours. Traveling from Garden City in December, expect slightly colder with lows of 29°F in Riverhead. Finish your sightseeing early on the 31st (Tue) so you can drive to Montauk.

Things to do in Riverhead

Outdoors · Parks · Beaches · Fun & Games

Side Trips

2
nights
Montauk

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. Start off your visit on the 1st (Wed): make a trip to Montauk Point Lighthouse. Keep things going the next day: admire the majestic nature at Hither Hills State Park, then contemplate the long history of Pollock-Krasner House and Study Center, then don't miss a visit to Gosman's Restaurant, and finally admire the majestic nature at Montauk Point State Park.

To see other places to visit, ratings, reviews, and tourist information, read Montauk trip itinerary planner.

Traveling by car from Riverhead to Montauk takes 1.5 hours. Plan for somewhat warmer nights when traveling from Riverhead in December since evenings lows in Montauk dip to 37°F. Finish your sightseeing early on the 2nd (Thu) to allow enough time to drive back home.

Things to do in Montauk

Parks · Nature · Historic Sites

Side Trip

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.