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Key West Historic Sites

key west dry tortugas ferry

Yankee Freedom III

2 Stop 2

Experience a journey like no other aboard the Yankee Freedom III. Take your comfortable seat and enjoy the relaxing ride to the Dry Tortugas National Park Fort Jefferson, just 70 miles west of Key West. The Yankee Freedom III is recognized for its speed and luxurious accommodations and for transporting thousands of visitors annually to the beautiful collection of islands called the Dry Tortugas.

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key west oldest house museum

Oldest House Museum

4 Stop 4 Free

The oldest house in South Florida was built in 1829 by Captain Francis Watlington who was, among other things, a wrecker. Watlington and his wife and their seven (of nine) surviving daughters lived in the house for many decades. A beautiful example of the kind of colonial architecture found in the Caribbean, the house is now a museum that welcomes visitors from around the world. Guests see gold that was salvaged from shipwrecks, paintings, model ships and a separate kitchen. Furnishings, carpets and the house décor all reflect the era of the wreckers and their success that made Key West the richest city in America at one time. There’s also a lovely garden with benches offering a shady spot to rest and relax. Learn a little history, admire the ancient architecture and more at the Oldest House Museum.

key west east martello fort robert the doll

East Martello Fort/ Robert The Doll

9 Stop 9

The East Martello Fort, complete with an eight-foot thick granite wall, was built during the Civil War Era to withstand any bombardment but was never completed and never saw any hostile action. The casemates, citadel and courtyard today make up the museum. Among its collection are Key West artifacts, historical records and military memorabilia. Also on display are the state’s largest collections of painted wood carvings and drawings by Mario Sanchez. In addition, the fort is also home to Robert the Doll, the most famous haunted plaything in the world.

key west customs house

Customs House Museum

1 Stop 1

For a bit of history and a look at how Key West got to where it is today, stop in at the Key West Museum of Art and History inside the Custom House. Built in 1891, the Custom House had many uses including a post office, court house and government center. Today, after a $9 million restoration, the beautiful red brick building is as glorious as it was back in the day and is home to moving works of art that portray the colorful past of Key West and historic national events.

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key west truman little white house

Truman Little White House

1 Stop 1

A place where an array of leaders, legendary inventors, dignitaries, visionaries and many prestigious visitors were drawn to throughout its history, Key West’s Harry S. Truman Little White House holds a special place in the history of America. Constructed in 1890 to serve as the naval station’s command headquarters during the Spanish-American War, World War I and World War II, this historic site later became the second White House.

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key west lighthouse

Key West Lighthouse

5 Stop 5

If you’re up for a climb, you’ll be rewarded with stunning views of Key West and the ocean. The Key West Lighthouse was built in 1825 to help the many ships entering the port avoid the hazardous reefs. Today, you can climb the 88 iron steps to the top of the tower for a scenic look at what the lighthouse keepers watched over for more than 120 years. Tour the grounds to see the Keeper’s Quarters which have been restored to their original charm and view the displays of nautical artifacts, antique furnishings, maps and vintage photos.

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