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Key West Theater

Waterfront Playhouse by Judy Bradford Waterfront Playhouse by Judy Bradford

Key West is home to four theaters showcasing live performances of new and critically-acclaimed works.

The Red Barn Theatre has become a cultural cornerstone for the Key West community while building a national reputation for creating BIG things in a small space. Many well-known and very talented people are a part of the Red Barn’s story. Richard Wilbur, the former U.S. Poet Laureate, worked with the Red Barn to produce his Moliere translations and Shel Silverstein, the gifted children’s writer, gave the Red Barn Theatre carte blanche to produce many of his very grown-up plays. Jimmy Buffett, Philip Burton, Terrence McNally, Jerry Herman, and Tennessee Williams have all made the Red Barn Theatre a part of their cultural experiences in Key West. Key West’s beloved Red Barn Theatre continues to produce regional premieres of vibrant new plays and musicals. Whether premiering new scripts or working with the classics, Red Barn Theatre has spent the last thirty-two years committed to nurturing artistic excellence within the local and national arts community. For more information visit or call (305) 296-9911.

The Waterfront Playhouse has been entertaining Key West audiences for over 70 years. Located in the heart of Key West’s historic Mallory Square, this not-for-profit, professional theater attracts locals and tourists with a wide range of theatrical fare. The Playhouse is an intimate 150-seat theater located steps from Key West’s nightly sunset celebration. The Playhouse utilizes Key West’s rich talent pool of actors, directors and designers, as well as attracting internationally known luminaries including Kelly McGillis, Donna McKechnie, Charles Busch, Terrence McNally, Israel Horowitz and Carl Hiaasen. Recent hit productions at the Playhouse include Lend Me a Tenor, Dirty Rotten Scoundrels, Doubt; Twelve Angry Men, The Full Monty, Reefer Madness, Regrets Only; The Musical of Musicals; Urinetown, BitchSlap!, Gore Vidal’s The Best Man; Equus and the world premiere of Carl Hiaasen’s Lucky You, as well as many others. For more information visit or call (305) 294-5015.