31 days in Long Island Itinerary

31 days in Long Island Itinerary

Created using Inspirock Long Island route maker

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Plan created by another user. Make it yours
Drive
1
Wantagh
— 5 nights
Drive
2
Fire Island
— 6 nights
Drive
3
Mattituck
— 7 nights
Drive
4
Shelter Island
— 5 nights
Drive
5
Montauk
— 7 nights
Drive

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5
nights
Wantagh

Wantagh is a hamlet and census-designated place (CDP) in the Town of Hempstead in Nassau County on Long Island, New York, United States. Explore the numerous day-trip ideas around Wantagh: Bayard Cutting Arboretum (in Great River), Planting Fields Arboretum State Historic Park (in Oyster Bay) and Sands Point Preserve (in Port Washington). Next up on the itinerary: enjoy the sand and surf at Jones Beach State Park, take a memorable tour with The Adventure Park at Long Island, stroll through Long Beach, and appreciate the extensive heritage of Argyle Park.

To find ratings, reviews, more things to do, and more tourist information, refer to the Wantagh trip builder.

Philadelphia to Wantagh is an approximately 2.5-hour car ride. September in Wantagh sees daily highs of 77°F and lows of 61°F at night. Wrap up your sightseeing on the 23rd (Wed) early enough to drive to Fire Island.

Things to do in Wantagh

Parks · Outdoors · Historic Sites · Tours

Side Trips

6
nights
Fire Island

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: Patchogue (Fire Island National Seashore & Amazing Olive), Holtsville Ecology Site (in Holtsville) and Long Island Skydiving Center (in Shirley). There's lots more to do: visit a coastal fixture at Fire Island Lighthouse, contemplate the long history of Sagamore Hill National Historic Site, look for all kinds of wild species at Avalon Park & Preserve, and explore the world behind art at Parrish Art Museum.

Planning Fire Island trip won't be overwheling when you use's Insprock itinerary maker.

Getting from Wantagh to Fire Island by car takes about 1.5 hours. In September in Fire Island, expect temperatures between 77°F during the day and 60°F at night. Finish your sightseeing early on the 29th (Tue) to allow enough time to drive to Mattituck.

Things to do in Fire Island

Parks · Nature · Museums · Historic Sites

Side Trips

7
nights
Mattituck

Mattituck is a hamlet and census-designated place (CDP) in Suffolk County, New York, United States. New Vine Wine Tours has been added to your itinerary. Next up on the itinerary: learn about winemaking at Macari Vineyards, learn the secrets of beer at Brew Crew Cycles, get some fabulous bargains at Tanger Outlets Riverhead, and look for all kinds of wild species at Quogue Wildlife Refuge.

To plan Mattituck vacation without wasting time, ask Inspirock to design an itinerary.

You can drive from Fire Island to Mattituck in 2 hours. Expect little chillier evenings in Mattituck when traveling from Fire Island in September, with lows around 55°F. Cap off your sightseeing on the 6th (Tue) early enough to go by car to Shelter Island.

Things to do in Mattituck

Wineries · Tours · Shopping · Parks

Side Trips

5
nights
Shelter Island

Explore Shelter Island's surroundings by going to Greenport (Kontokosta Winery, Wine Tours & Tastings, &more), Southold (The Old Field Vineyards, Sparkling Pointe Vineyards & Winery, &more) and Sag Harbor (Sag Harbor Whaling and Historical Museum, Custom House Museum, &more).

To find where to stay, maps, more things to do, and more tourist information, you can read our Shelter Island trip maker site.

You can drive from Mattituck to Shelter Island in an hour. Traveling from Mattituck in October, you can expect nighttime temperatures to be somewhat warmer in Shelter Island, with lows of 52°F. Wrap up your sightseeing on the 11th (Sun) to allow time to drive to Montauk.

Things to do in Shelter Island

Wineries · Theme Parks · Tours · Museums

Side Trips

7
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. Explore the numerous day-trip ideas around Montauk: East Hampton (LongHouse Reserve & Guild Hall) and Wolffer Estate Vineyard (in Sagaponack). Next up on the itinerary: make a trip to Montauk Point Lighthouse, enjoy the sand and surf at Ditch Plains, admire the majestic nature at Shadmoor State Park, and pause for some serene contemplation at St. Therese of Lisieux Catholic Church.

To see ratings, photos, traveler tips, and other tourist information, read Montauk visit planning app.

Getting from Shelter Island to Montauk by car takes about 1.5 hours. October in Montauk sees daily highs of 65°F and lows of 53°F at night. Finish up your sightseeing early on the 18th (Sun) so you can go by car back home.

Things to do in Montauk

Parks · Outdoors · Nature · 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.