60 days in Long Island Itinerary

60 days in Long Island Itinerary

Created using Inspirock Long Island sightseeing planner

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Make it your trip
Drive
1
Garden City
— 14 nights
Drive
2
Montauk
— 14 nights
Drive
3
Riverhead
— 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. You'll find plenty of places to visit near Garden City: Bay Shore (Gardiner County Park & Sagtikos Manor), Babylon (Captree State Park & Argyle Park) and Tanger Outlets Deer Park (in Deer Park). Pack the 1st (Sat) with family-friendly diversions at Adventureland. The adventure continues: examine the collection at Cradle of Aviation Museum, stroll around Norman J. Levy Park & Preserve, admire the natural beauty at Planting Fields Arboretum State Historic Park, and browse the different shops at Roosevelt Field.

To see photos, other places to visit, maps, and more tourist information, refer to the Garden City driving holiday planner.

Philadelphia to Garden City is an approximately 2.5-hour car ride. When traveling from Philadelphia in April, plan for a bit cooler days and about the same nights in Garden City: temperatures range from 59°F by day to 43°F at night. Finish up your sightseeing early on the 6th (Thu) so you can travel to Montauk.

Things to do in Garden City

Parks · Museums · Historic Sites · Wildlife

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. Venture out of the city with trips to Elizabeth A. Morton National Wildlife Refuge (in Noyack), Sag Harbor (Sag Harbor Marine Park, Custom House Museum, &more) and East Hampton (LongHouse Reserve, Home Sweet Home Museum, &more). The adventure continues: enjoy the sea views from Montauk Point Lighthouse, steep yourself in history at Camp Hero State Park, take in the waterfront activity at Star Island Yacht Club and Marina, and admire the majestic nature at Shadmoor State Park.

To see where to stay, ratings, reviews, and more tourist information, go to the Montauk trip itinerary planner.

Drive from Garden City to Montauk in 2 hours. In May in Montauk, expect temperatures between 65°F during the day and 50°F at night. Finish your sightseeing early on the 20th (Thu) to allow enough time to drive to Riverhead.

Things to do in Montauk

Parks · Outdoors · Museums · Beaches

Side Trips

Riverhead

— 16 nights
Riverhead is a town within Suffolk County, New York, on the north shore of Long Island. Explore Riverhead's surroundings by going to Massage Envy (in Rocky Point), Patchogue (Amazing Olive, Fire Island National Seashore, &more) and William Floyd Estate (in Mastic Beach). And it doesn't end there: observe the fascinating underwater world at Long Island Aquarium, identify plant and animal life at Holtsville Ecology Site, learn the secrets of beer at Brew Crew Cycles, and learn about winemaking at Paumanok Vineyards.

For photos, reviews, where to stay, and other tourist information, refer to the Riverhead planner.

Traveling by car from Montauk to Riverhead takes 1.5 hours. In May in Riverhead, expect temperatures between 66°F during the day and 46°F at night. Finish your sightseeing early on the 5th (Sat) so you can drive to Fire Island.

Things to do in Riverhead

Wineries · Parks · Wildlife · Breweries & Distilleries

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. Get out of town with these interesting Fire Island side-trips: Orient (Orient by the Sea Marina & Orient Beach State Park), Hampton Bays (Church of St. Rosalie, House of Wellness, &more) and Southampton (The Thomas Halsey Homestead, Cooper's Beach, &more). There's much more to do: go for a stroll along the water at Sailors Haven Visitor Center, enjoy the sea views from Fire Island Lighthouse, enjoy the sand and surf at Ocean Road Beach, and walk around Robert Moses State Park.

For more things to do, ratings, other places to visit, and more tourist information, refer to the Fire Island trip planner.

You can drive from Riverhead to Fire Island in 1.5 hours. In June, daytime highs in Fire Island are 78°F, while nighttime lows are 61°F. You will leave for home on the 20th (Sun).

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.