4 days in Long Island Itinerary

4 days in Long Island Itinerary

Created using Inspirock Long Island trip itinerary builder

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Route & dates

4 days in Long Island Itinerary

Start: Chicago
Fly + Drive:  11​h 15​min
1
Southold
— 2 nights
Drive:  1​h 45​min
2
Floral Park
— 1 night
Drive + Fly:  9​h 30​min
End: Chicago

2
nights
Southold

Southold ©
The Town of Southold is one of ten towns in Suffolk County, New York, United States. Start off your visit on the 8th (Sun): make a trip to Montauk Point Lighthouse, then make a trip to St. Therese of Lisieux Catholic Church, and then examine the collection at Mystic Seaport Museum. Get ready for a full day of sightseeing on the 9th (Mon): pause for some serene contemplation at Our Lady of Poland Catholic Church, look for all kinds of wild species at Quogue Wildlife Refuge, and then enjoy the sand and surf at Cupsogue Beach County Park.

Inspirock's itinerary builder makes planning a Southold trip simple and quick.

Chicago to Southold is an approximately 11.5-hour combination of flight and car. You can also drive. The time zone changes from Central Standard Time (CST) to Eastern Standard Time (EST), which is usually a 1 hour difference. While traveling from Chicago, expect a bit cooler days and about the same nights in Southold, ranging from highs of 72°F to lows of 59°F. Finish your sightseeing early on the 9th (Mon) to allow enough time to travel to Floral Park.

Things to do in Southold

Parks Historic Sites Beaches

Side Trips

Montauk, Mystic Seaport Museum, Our Lady of Poland Catholic Church, Cupsogue Beach County Park, Quogue Wildlife Refuge
Highlights from your plan
Cupsogue Beach County Park ©
Cupsogue Beach County Park
Mystic Seaport Museum ©
Mystic Seaport Museum
Montauk Point Lighthouse ©
Montauk Point Lighthouse

1
night
Floral Park

Floral Park ©
Floral Park is an incorporated village in Nassau County, New York, United States, on Long Island. On the 10th (Tue), pause for some serene contemplation at Cathedral of the Incarnation and then kick back and relax at Point Lookout Beach.

To find where to stay, maps, traveler tips, and tourist information, refer to the Floral Park online route planner .

Traveling by car from Southold to Floral Park takes 2 hours. Traveling from Southold in September, you will find days in Floral Park are a bit warmer (78°F), and nights are about the same (62°F). Finish your sightseeing early on the 10th (Tue) so you can travel back home.

Things to do in Floral Park

Parks Beaches Outdoors

Side Trips

Point Lookout Beach, Cathedral of the Incarnation
Highlights from your plan
Point Lookout Beach ©
Point Lookout Beach
Cathedral of the Incarnation ©
Cathedral of the Incarnation

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