29 days in Long Island Itinerary

29 days in Long Island Itinerary

Created using Inspirock Long Island itinerary planner

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Plan created by another user. Make it yours
1
Bohemia
— 7 nights
2
Montauk
— 7 nights
3
Southold
— 7 nights
4
Fire Island
— 7 nights

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7
nights
Bohemia

Bohemia ©
Bohemia is a hamlet (and census-designated place) in Suffolk County, New York, United States. Deepen your sense of the past at sights like Old Bethpage Village Restoration and Calverton National Cemetery. Do some cultural sightseeing at Long Island Museum of American Art, History and Carriages and Long Island Maritime Museum. Get out of town with these interesting Bohemia side-trips: William Floyd Estate (in Mastic Beach), The Whaling Museum & Education Center (in Cold Spring Harbor) and Walt Whitman Birthplace (in Huntington Station). There's lots more to do: play a few rounds at Bethpage Black, kick back and relax at Tobay Beach, stroll through Corey Beach, and get engrossed in the history at American Airpower Museum.

For where to stay, other places to visit, ratings, and more tourist information, refer to the Bohemia route planning tool.

New York City to Bohemia is an approximately 1.5-hour car ride. In July, daytime highs in Bohemia are 84°F, while nighttime lows are 69°F. Finish your sightseeing early on the 29th (Wed) to allow enough time to travel to Montauk.

Things to do in Bohemia

Parks · Outdoors · Beaches · Historic Sites

Side Trips

Highlights from your plan
Belmont Lake State Park ©
Belmont Lake State Park
Long Island Maritime Museum ©
Long Island Maritime Museum
William Floyd Estate ©
William Floyd Estate

7
nights
Montauk

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. Visit Kirk Park Beach and Ocean Road Beach for some beach relaxation. Step off the beaten path and head to Shadmoor State Park and Sag Harbor Whaling and Historical Museum. Venture out of the city with trips to Bridgehampton (South Fork Natural History Museum, Children's Museum of The East End, &more), Sag Harbor (Sag Harbor Marine Park, Foster Memorial Beach, &more) and East Hampton (Home Sweet Home Museum & Guild Hall). There's lots more to do: stroll through Gin Beach, contemplate the long history of Pollock-Krasner House and Study Center, make a trip to St. Therese of Lisieux Catholic Church, and admire the majestic nature at Montauk Downs State Park.

For where to stay, other places to visit, more things to do, and tourist information, read our Montauk online tour planner.

You can drive from Bohemia to Montauk in 1.5 hours. In July in Montauk, expect temperatures between 80°F during the day and 68°F at night. Wrap up your sightseeing on the 5th (Wed) early enough to drive to Southold.

Things to do in Montauk

Museums · Parks · Outdoors · Beaches

Side Trips

Highlights from your plan
Sag Harbor Whaling and Historical Museum ©
Sag Harbor Whaling and Historical Museum
The Leiber Collection ©
The Leiber Collection
Guild Hall ©
Guild Hall

7
nights
Southold

Southold ©
The Town of Southold is one of ten towns in Suffolk County, New York, United States. Head to Alex Ferrone Gallery and Greenport Farmers' Market, Inc.for plenty of shopping. Visiting Boat Tours & Water Sports and Elizabeth A. Morton National Wildlife Refuge will get you outdoors. You'll find plenty of places to visit near Southold: Quogue Wildlife Refuge (in Quogue) and Woodside Orchards (in Aquebogue). There's lots more to do: do a tasting at Raphael Winery, enjoy the sand and surf at Orient Beach State Park, and enjoy the sea views from Horton Point Lighthouse Nautical Museum.

To find other places to visit, where to stay, and tourist information, read Southold trip planner.

Traveling by car from Montauk to Southold takes 1.5 hours. In August, daily temperatures in Southold can reach 77°F, while at night they dip to 64°F. Finish your sightseeing early on the 12th (Wed) to allow enough time to travel to Fire Island.

Things to do in Southold

Wineries · Parks · Wildlife · Outdoors

Side Trips

Highlights from your plan
Osprey's Dominion Vineyards ©
Osprey's Dominion Vineyards
Orient Beach State Park ©
Orient Beach State Park
Quogue Wildlife Refuge ©
Quogue Wildlife Refuge

7
nights
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. Get in touch with nature at The Sunken Forest and Sailors Haven Visitor Center. Get a sense of the local culture at Duck Walk Vineyard and Southampton History Museum. Explore Fire Island's surroundings by going to Hempstead Lake State Park (in Hempstead), Southampton (Our Lady of Poland Catholic Church, Shinnecock East County Park, &more) and Meschutt Beach (in Hampton Bays). And it doesn't end there: kick back and relax at Kismet Beach, stroll through Lido Beach, stroll around Eisenhower Park, and admire the natural beauty at Hicks Nurseries.

To see ratings, photos, more things to do, and other tourist information, go to the Fire Island road trip planning app.

Traveling by journey from Southold to Fire Island takes 2 hours. In August, plan for daily highs up to 82°F, and evening lows to 66°F. Finish your sightseeing early on the 19th (Wed) to allow enough time to travel back home.

Things to do in Fire Island

Parks · Outdoors · Beaches · Nature

Side Trips

Highlights from your plan
The Sunken Forest ©
The Sunken Forest
Meschutt Beach ©
Meschutt Beach
Norman J. Levy Park & Preserve ©
Norman J. Levy Park & Preserve

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