29 days in Long Island Itinerary

29 days in Long Island Itinerary

Created using Inspirock Long Island itinerary maker

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

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Fire Island

— 6 nights
Fire Island is the large center island of the outer barrier islands parallel to the south shore of Long Island, New York. Appreciate the collections at Parrish Art Museum and Southampton Arts Center. Escape the urban bustle at Long Beach and Ponquogue Beach. Get out of town with these interesting Fire Island side-trips: Southampton (Shinnecock East County Park, Southampton History Museum, &more), Hampton Bays (Church of St. Rosalie & Meschutt Beach) and Lido Beach (in Lido Beach). Next up on the itinerary: visit a coastal fixture at Fire Island Lighthouse, get to know the fascinating history of Freeport's Nautical Mile, tour the pleasant surroundings at Ocean Beach, and delve into the lush surroundings at The Sunken Forest.

To find maps, ratings, more things to do, and tourist information, refer to the Fire Island online day trip planner.

New York City to Fire Island is an approximately 2-hour car ride. In July, daytime highs in Fire Island are 84°F, while nighttime lows are 69°F. Cap off your sightseeing on the 28th (Tue) early enough to go by car to Southold.

Things to do in Fire Island

Parks · Outdoors · Beaches · Historic Sites

Side Trips

Southold

— 7 nights
The Town of Southold is one of ten towns in Suffolk County, New York, United States. Popular historic sites such as Horton Point Lighthouse Nautical Museum and Oysterponds Historical Society are in your itinerary. Sannino Bella Vita Vineyard and Clovis Point are good opportunities to explore the local culture. Explore the numerous day-trip ideas around Southold: Woodside Orchards (in Aquebogue) and Quogue Wildlife Refuge (in Quogue). There's more to do: learn about winemaking at Pellegrini Vineyards and enjoy the sand and surf at Orient Beach State Park.

To find other places to visit, ratings, more things to do, and other tourist information, use the Southold trip itinerary maker.

Getting from Fire Island to Southold by car takes about 2 hours. When traveling from Fire Island in July, plan for little chillier days and about the same nights in Southold: temperatures range from 79°F by day to 67°F at night. Cap off your sightseeing on the 4th (Tue) early enough to go by car to Montauk.

Things to do in Southold

Wineries · Parks · Museums · Wildlife

Side Trips

Montauk

— 8 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. Deepen your sense of the past at sights like Montauk Point Lighthouse and St. Therese of Lisieux Catholic Church. For shopping fun, head to Main Beach or Round Swamp Farm. Change things up with these side-trips from Montauk: East Hampton (Home Sweet Home Museum & Guild Hall), Sag Harbor (Havens Beach, Foster Memorial Beach, &more) and Bridgehampton (Children's Museum of The East End, Channing Daughters Winery, &more). There's still lots to do: steep yourself in history at Pollock-Krasner House and Study Center, admire the majestic nature at Shadmoor State Park, get engrossed in the history at Second House Museum, and examine the collection at The Leiber Collection.

For reviews, where to stay, ratings, and more tourist information, refer to the Montauk trip planning site.

Traveling by car from Southold to Montauk takes 1.5 hours. In August in Montauk, expect temperatures between 79°F during the day and 66°F at night. Wrap up your sightseeing on the 12th (Wed) to allow time to travel to Bohemia.

Things to do in Montauk

Outdoors · Parks · Museums · Beaches

Side Trips

Bohemia

— 7 nights
Bohemia is a hamlet (and census-designated place) in Suffolk County, New York, United States. Take a break from the city and head to Fire Island National Seashore and Cupsogue Beach County Park. Your inner history buff will appreciate Sagamore Hill National Historic Site and William Floyd Estate. Venture out of the city with trips to Pike's Beach (in Westhampton Beach), Tobay Beach (in Massapequa) and Gilgo Beach (in Babylon). The adventure continues: stroll through Avalon Park & Preserve, immerse yourself in nature at Connetquot River State Park Preserve, kick back and relax at Corey Beach, and explore the different monuments and memorials at Calverton National Cemetery.

For reviews, more things to do, maps, and more tourist information, go to the Bohemia trip itinerary planning site.

Drive from Montauk to Bohemia in 1.5 hours. In August in Bohemia, expect temperatures between 82°F during the day and 66°F at night. Wrap up your sightseeing on the 19th (Wed) to allow time to travel back home.

Things to do in Bohemia

Parks · Outdoors · Beaches · Nature

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.