8 days in Long Island Itinerary

8 days in Long Island Itinerary

Created using Inspirock Long Island attractions planner

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Make it your trip
Drive
1
Southold
— 3 nights
Drive
2
Sag Harbor
— 3 nights
Drive
3
Fire Island
— 1 night
Drive

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Southold

— 3 nights
The Town of Southold is one of ten towns in Suffolk County, New York, United States. You'll discover tucked-away gems like Alex Ferrone Gallery and Horton Point Lighthouse Nautical Museum. Get some cultural insight at McCall Wines and Clovis Point. Venture out of the city with trips to Aquebogue (Woodside Orchards & North Fork Chocolate Company). There's more to do: do a tasting at Coffee Pot Cellars Tasting Room and experience rural life at The East End Mushroom Company.

For where to stay, traveler tips, photos, and other tourist information, go to the Southold road trip website.

New York City to Southold is an approximately 2-hour car ride. Expect slightly colder temperatures when traveling from New York City in July; daily highs in Southold reach 79°F and lows reach 67°F. Cap off your sightseeing on the 25th (Sat) early enough to travel to Sag Harbor.

Things to do in Southold

Wineries · Museums · Historic Sites · Shopping

Side Trips

Sag Harbor

— 3 nights
Sag Harbor is an incorporated village in Suffolk County, New York, United States, in the towns of East Hampton and Southampton. You'll get in some beach time at Foster Memorial Beach and Orient Beach State Park. Museum-lovers will get to explore Custom House Museum and Guild Hall. The adventure continues: tour the pleasant surroundings at Elizabeth A. Morton National Wildlife Refuge, browse the fresh offerings at Round Swamp Farm, do a tasting at Channing Daughters Winery, and examine the collection at Sag Harbor Whaling and Historical Museum.

To find other places to visit, more things to do, where to stay, and more tourist information, read our Sag Harbor online visit planner.

Getting from Southold to Sag Harbor by car takes about 1.5 hours. In July, daytime highs in Sag Harbor are 79°F, while nighttime lows are 67°F. Finish your sightseeing early on the 28th (Tue) to allow enough time to drive to Fire Island.

Things to do in Sag Harbor

Parks · Museums · Outdoors · Beaches

Side Trips

Fire Island

— 1 night
Fire Island is the large center island of the outer barrier islands parallel to the south shore of Long Island, New York. Kick off your visit on the 29th (Wed): stroll through Kismet Beach and then take a peaceful walk through The Sunken Forest.

To find other places to visit, maps, more things to do, and tourist information, go to the Fire Island road trip planning website.

Traveling by car from Sag Harbor to Fire Island takes 2 hours. In July in Fire Island, expect temperatures between 84°F during the day and 69°F at night. Cap off your sightseeing on the 29th (Wed) early enough to go by car back home.

Things to do in Fire Island

Parks · Outdoors · Beaches · Nature

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.