8 days in Long Island Itinerary

8 days in Long Island Itinerary

Created using Inspirock Long Island attractions planner

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Plan created by another user. Make it yours
1
Southold
— 3 nights
2
Sag Harbor
— 3 nights
3
Fire Island
— 1 night

S M T W T F S
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3
nights
Southold

Southold ©
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 The Old Field Vineyards. Get some cultural insight at Coffee Pot Cellars Tasting Room and Horton Point Lighthouse Nautical Museum. Venture out of the city with trips to Aquebogue (Woodside Orchards & North Fork Chocolate Company). There's more to do: relax in the rural setting at The East End Mushroom Company and learn about winemaking at McCall Wines.

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

Side Trips

Cutchogue, Riverhead, Peconic, Clovis Point, Laurel Lake Vineyard
Highlights from your plan
Coffee Pot Cellars Tasting Room ©
Coffee Pot Cellars Tasting Room
The Old Field Vineyards ©
The Old Field Vineyards
Alex Ferrone Gallery ©
Alex Ferrone Gallery

3
nights
Sag Harbor

Sag Harbor ©
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 Guild Hall and Custom House Museum. There's much more to do: identify plant and animal life at Elizabeth A. Morton National Wildlife Refuge, examine the collection at Sag Harbor Whaling and Historical Museum, steep yourself in history at Shelter Island Historical Society, and do a tasting at Channing Daughters Winery.

To find where to stay, ratings, traveler tips, and more tourist information, read our Sag Harbor online vacation planner.

Traveling by car from Southold to Sag Harbor takes 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) so you can travel to Fire Island.

Things to do in Sag Harbor

Parks · Museums · Beaches

Side Trips

East Hampton, Orient Beach State Park, Elizabeth A. Morton National Wildlife Refuge, Shelter Island Historical Society, Channing Daughters Winery
Highlights from your plan
Elizabeth A. Morton National Wildlife Refuge ©
Guild Hall ©
Guild Hall
Custom House Museum ©
Custom House Museum

1
night
Fire Island

Fire Island ©
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 journey 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 travel back home.

Things to do in Fire Island

Parks · Beaches · Outdoors
Highlights from your plan
The Sunken Forest ©
The Sunken Forest

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