60 days in Long Island Itinerary

60 days in Long Island Itinerary

Created using Inspirock Long Island travel planner

©
Make it your trip
Drive
1
Garden City
— 14 nights
Drive
2
Montauk
— 14 nights
Drive
3
Cutchogue
— 16 nights
Drive
4
Fire Island
— 15 nights
Drive

S M T W T F S
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
1
2
3
4
5
6
7
8
9
10
11
12

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. Get out of town with these interesting Garden City side-trips: Long Island Photo Gallery (in Islip), Babylon (Argyle Park & Captree State Park) and Our Lady of Grace Roman Catholic Church (in West Babylon). The adventure continues: see the interesting displays at Cradle of Aviation Museum, tour the pleasant surroundings at Bayard Cutting Arboretum, browse the exhibits of Sagamore Hill National Historic Site, and take in the architecture and atmosphere at Cathedral of the Incarnation.

To see photos, where to stay, maps, and tourist information, read Garden City online travel planner.

Philadelphia to Garden City is an approximately 2.5-hour car ride. While traveling from Philadelphia, expect slightly colder days and about the same nights in Garden City, ranging from highs of 59°F to lows of 43°F. Finish your sightseeing early on the 28th (Wed) so you can travel to Montauk.

Things to do in Garden City

Parks · Museums · Wildlife · Historic Sites

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. Change things up with these side-trips from Montauk: Bridgehampton (South Fork Natural History Museum, Channing Daughters Winery, &more), East Hampton (Home Sweet Home Museum, LongHouse Reserve, &more) and Sagaponack (Wolffer Estate Vineyard & Madoo Conservancy). There's lots more to do: enjoy the sea views from Montauk Point Lighthouse, walk around Navy Road Park, immerse yourself in nature at Montauk Point State Park, and get a taste of life in the country at Deep Hollow Ranch.

To find out how to plan a trip to Montauk, use our trip itinerary maker.

Traveling by car from Garden City to Montauk takes 2 hours. Expect a daytime high around 55°F in April, and nighttime lows around 41°F. Finish your sightseeing early on the 12th (Wed) so you can drive to Cutchogue.

Things to do in Montauk

Parks · Outdoors · Museums · Nature

Side Trips

Cutchogue

— 16 nights
Cutchogue is a hamlet and census-designated place (CDP) in Suffolk County, New York, United States. Get out of town with these interesting Cutchogue side-trips: Tanger Outlets Riverhead (in Riverhead), Shelter Island (Shelter Island Historical Society & Mashomack Preserve) and Calverton (Splish Splash & Calverton National Cemetery). There's much more to do: take in the exciting artwork at Alex Ferrone Gallery, make a trip to Congregation Tifereth Israel, do a tasting at Castello di Borghese / Hargrave Vineyard, and admire nature's wide array of creatures at Long Island Aquarium.

To find more things to do and tourist information, go to the Cutchogue road trip site.

Getting from Montauk to Cutchogue by car takes about 1.5 hours. In May, plan for daily highs up to 64°F, and evening lows to 52°F. Cap off your sightseeing on the 28th (Fri) early enough to go by car to Fire Island.

Things to do in Cutchogue

Wineries · Parks · Wildlife · Historic Sites

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. You'll find plenty of places to visit near Fire Island: Hampton Bays (Ponquogue Beach, House Of Wellness, &more), Corey Beach (in Blue Point) and Southampton (Southampton History Museum, Cooper's Beach, &more). The adventure continues: stroll through Sailors Haven Visitor Center, enjoy the sand and surf at Kismet Beach, walk around Shorefront Park, and take a peaceful walk through The Sunken Forest.

To find maps, more things to do, where to stay, and tourist information, read our Fire Island sightseeing planner.

You can drive from Cutchogue to Fire Island in 2 hours. In May, plan for daily highs up to 69°F, and evening lows to 51°F. On the 12th (Sat), you're off to 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.