29 days in Long Island Itinerary

29 days in Long Island Itinerary

Created using Inspirock Long Island itinerary planner

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Make it your trip
Drive
1
Bohemia
— 7 nights
Drive
2
Montauk
— 7 nights
Drive
3
Southold
— 7 nights
Drive
4
Fire Island
— 7 nights
Drive

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Bohemia

— 7 nights
Bohemia is a hamlet (and census-designated place) in Suffolk County, New York, United States. Deepen your sense of the past at sights like American Airpower Museum and Old Bethpage Village Restoration. Do some cultural sightseeing at Long Island Museum of American Art, History and Carriages and Argyle Park. Get out of town with these interesting Bohemia side-trips: The Whaling Museum & Education Center (in Cold Spring Harbor), Walt Whitman Birthplace (in Huntington Station) and William Floyd Estate (in Mastic Beach). There's lots more to do: explore the different monuments and memorials at Calverton National Cemetery, immerse yourself in nature at Connetquot River State Park Preserve, see the interesting displays at Long Island Maritime Museum, and enjoy the sand and surf at Corey Beach.

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

Montauk

— 7 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. Visit Kirk Park Beach and Gin Beach for some beach relaxation. Step off the beaten path and head to Shadmoor State Park and Montauk Downs State Park Golf Course. Venture out of the city with trips to Sag Harbor (Sag Harbor Marine Park, Sag Harbor Whaling and Historical Museum, &more), East Hampton (Home Sweet Home Museum & Guild Hall) and Bridgehampton (Ocean Road Beach, South Fork Natural History Museum, &more). There's still lots to do: admire the majestic nature at Montauk Downs State Park, pick up some local products at Round Swamp Farm, get engrossed in the history at Second House Museum, and walk around Navy Road Park.

To find maps, more things to do, reviews, and other tourist information, use the Montauk itinerary builder website.

You can drive from Bohemia to Montauk in 1.5 hours. In July, daytime highs in Montauk are 80°F, while nighttime lows are 68°F. Wrap up your sightseeing on the 5th (Wed) to allow time to drive to Southold.

Things to do in Montauk

Museums · Parks · Outdoors · Beaches

Side Trips

Southold

— 7 nights
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 Orient Beach State Park 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 more to do: do a tasting at The Old Field Vineyards and examine the collection at Horton Point Lighthouse Nautical Museum.

To find traveler tips, other places to visit, where to stay, and more tourist information, you can read our Southold online route planner.

You can drive from Montauk to Southold in 1.5 hours. In August in Southold, expect temperatures between 77°F during the day and 64°F at night. Cap off your sightseeing on the 12th (Wed) early enough to go by car to Fire Island.

Things to do in Southold

Wineries · Parks · Wildlife · Outdoors

Side Trips

Fire Island

— 7 nights
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 Southampton (Our Lady of Poland Catholic Church, Shinnecock East County Park, &more), Meschutt Beach (in Hampton Bays) and Hempstead Lake State Park (in Hempstead). 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 car 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 drive back home.

Things to do in Fire Island

Parks · Beaches · Outdoors · Wildlife

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.