54 days in Long Island Itinerary

54 days in Long Island Itinerary

Created using Inspirock Long Island journey planner

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Make it your trip
Drive
1
Freeport
— 13 nights
Drive
2
Montauk
— 14 nights
Drive
3
Riverhead
— 14 nights
Drive
4
Fire Island
— 12 nights
Drive

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Freeport

— 13 nights
Freeport is a village in the town of Hempstead, Nassau County, New York, USA, on the South Shore of Long Island. Get out of town with these interesting Freeport side-trips: Huntington (Caumsett State Park & Book Revue), Northport Village Park (in Northport) and White Post Farms (in Melville). Pack the 13th (Tue) with family-friendly diversions at Adventureland. There's still lots to do: cast your line with a fishing tour, take in nature's colorful creations at Planting Fields Arboretum State Historic Park, have fun and explore at Long Island Children's Museum, and stroll around Norman J. Levy Park & Preserve.

To see maps, reviews, photos, and more tourist information, go to the Freeport trip planner.

Philadelphia to Freeport is an approximately 2.5-hour car ride. While traveling from Philadelphia, expect slightly colder days and about the same nights in Freeport, ranging from highs of 58°F to lows of 42°F. Finish your sightseeing early on the 21st (Wed) so you can travel to Montauk.

Things to do in Freeport

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. Explore Montauk's surroundings by going to Sagaponack (Wolffer Estate Vineyard & Madoo Conservancy), Bridgehampton (Bridge Gardens, Channing Daughters Winery, &more) and Sag Harbor (Sag Harbor Marine Park, Custom House Museum, &more). Next up on the itinerary: visit a coastal fixture at Montauk Point Lighthouse, wander the wide-open spaces of Deep Hollow Ranch, admire the majestic nature at Hither Hills State Park, and tour the pleasant surroundings at Camp Hero State Park.

To find ratings, photos, and tourist information, read Montauk trip itinerary builder website.

Drive from Freeport to Montauk in 2 hours. In April in Montauk, expect temperatures between 55°F during the day and 41°F at night. Finish your sightseeing early on the 5th (Wed) to allow enough time to drive to Riverhead.

Things to do in Montauk

Parks · Outdoors · Museums · Nature

Side Trips

Riverhead

— 14 nights
Riverhead is a town within Suffolk County, New York, on the north shore of Long Island. Explore Riverhead's surroundings by going to Lenz Winery (in Peconic), Southold (Custer Institute & Observatory & Mattebella Vineyards) and Stony Brook (Long Island Museum of American Art, History and Carriages & Avalon Park & Preserve). There's still lots to do: admire nature's wide array of creatures at Long Island Aquarium, identify plant and animal life at Bayard Cutting Arboretum, revel in the low prices at Tanger Outlets Riverhead, and awaken your taste buds at some of the top wineries in the area.

To find where to stay, more things to do, ratings, and more tourist information, you can read our Riverhead trip itinerary maker app.

Drive from Montauk to Riverhead in 1.5 hours. In May in Riverhead, expect temperatures between 66°F during the day and 46°F at night. Wrap up your sightseeing on the 19th (Wed) to allow time to drive to Fire Island.

Things to do in Riverhead

Wineries · Parks · Wildlife · Historic Sites

Side Trips

Fire Island

— 12 nights
Fire Island is the large center island of the outer barrier islands parallel to the south shore of Long Island, New York. Change things up with these side-trips from Fire Island: Orient (Orient by the Sea Marina & Orient Beach State Park), Water Mill (Parrish Art Museum & Duck Walk Vineyard) and Southampton (Southampton History Museum, Cooper's Beach, &more). There's still lots to do: look for all kinds of wild species at Sailors Haven Visitor Center, pause for some serene contemplation at Church of St. Rosalie, admire the majestic nature at Robert Moses State Park, and enjoy the sand and surf at Mecox Beach.

To find ratings, other places to visit, photos, and other tourist information, read our Fire Island tour itinerary builder tool.

Getting from Riverhead to Fire Island by car takes about 1.5 hours. Expect a daytime high around 69°F in May, and nighttime lows around 51°F. Wrap up your sightseeing on the 31st (Mon) early enough to travel back 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.