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Top Rated Attractions in Key West

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Waterfront Playhouse

Named "The Best Professional Theater in Florida" by Florida Monthly Magazine in 2010 and 2011, The Waterfront Playhouse is a not-for-profit, professional theater located on historic Mallory Square in Old Town Key West. The theater attracts locals and tourists alike with a wide range of comedies, dramas, musicals, concerts, and world premieres. The Playhouse utilizes Key West's rich talent pool of actors, directors and designers, as well as attracting internationally known luminaries.

The Ernest Hemingway Home & Museum

The Hemingway Home & Museum was the residence of the renowned author Ernest Hemingway. Hemingway was known both for his grander-than-life personality and his amazing writing, including the books The Sun Also Rises and Farewell to Arms. The rooms and the collections on display give you an insight into the life of this famous writer. Keep a look out for the museum's many polydactyl (six-toed) cats that are rumored to be descendants of Hemingway's pet cat Snow White.

Tropic Cinema

For movie buffs, this cinema serves every purpose. Showcasing award-winning films and conducting courses in digital media and other areas, the Tropic Cinema has helped create awareness about cultures globally. It also hosts birthday parties, anniversaries and other occasions. Festive occasions call for a celebration and this is the place to be! See website for showtimes, ticketing info and more.

Mallory Square

Located by the historic Key West waterfront, this open-air marketplace and entertainment complex is a great place to start or end your visit to Key West. Known for its magnificent sunsets, the area is also home to many shops, including Shell Warehouse, Key West Sponge Market and Caribbean Cargo. The Square also features daily entertainment, which includes guitar music, juggling, and animal performances. Local sightseeing tours also depart from the Square.

Harry S. Truman Little White House

Nestled in the recesses of the historic Old Town, the Little White House is a startling canopy of pristine white, which lends deep insights into the Truman Presidency. Formerly a naval base which served as the White House of America for the winter session until 1952 , this site is more like a breathing museum entrenched in a long-standing military history. To this day, functions, meetings and private events are held here, whereas elaborate tours unfold layers of the house's presidential and political history. Part of the U.S. National Register of Historic Places, this white-washed house yet retains some of its ancient features like well-furnished spaces including bedrooms and dining halls, treasured documents and opulent furniture. Harry S. Truman Little White House is an integral edifice etched on the pages of America's political history.

Sloppy Joe's

Founded in 1933 on the day Prohibition was repealed, this famous bar became one of author Ernest Hemingway's favorite drinking spots. In fact, it is rumored that Hemingway even came up with the name "Sloppy Joe's." Nowadays, the bar has a very casual atmosphere, hosts live bands, and serves good meals, including the original Sloppy Joe sandwich. With live entertainment and a lively crowd, this is one of the best parties in town. It is also the home of a Hemingway look-alike contest.

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