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January 19 – February 20, 2027 · Tuesdays–Saturdays at 7:30pm Red Barn Theatre, 319 Duval Street (rear) The Red Barn follows its holiday show with Dracula: A Comedy of Terrors, the Gordon Greenberg and Steve Rosen send-up that became an off-Broadway hit and has been working its way through regional theaters ever since. The premise […] 
Featured
2027 Key West Food and Wine Festival January 27–31, 2027 5 continents ~ 5 wines ~ 5 stories ~ 5 dishes ~ 5 chefs Welcome to Key West Food & Wine Festival 2027 A curated journey through the culinary heritage of five continents, featuring world-renowned chefs, their signature dishes, and the legendary wines that define […] 
January 28 – February 6, 2027 Waterfront Playhouse, Mallory Square, 407 Wall Street The Waterfront's mainstage returns to Paul Slade Smith, whose The Angel Next Door played there previously, with Unnecessary Farce. Two cops have set up a sting in a cheap motel, hoping to catch the mayor taking a bribe. There are two adjoining […] |
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Monday, February 1, 2027 Doors 6:30pm, Show 7:30pm · Tennessee Williams Theatre The New York Gilbert & Sullivan Players bring their production of  to Key West this February. NYGASP has been the country's leading Gilbert & Sullivan repertory company for more than fifty years, and Pirates is the piece they're best known for — a […] |
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Tuesday, February 9, 2027 Doors 5:30pm, Show 6:30pm · Tennessee Williams Theatre Afrique en Cirque comes to Key West as part of the Tennessee Williams Theatre's new Family Fun Series, a slate of shows programmed for audiences of all ages. It's the signature production of Cirque Kalabanté, the company founded by Guinean acrobat Yamoussa Bangoura, […] |
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Thursday, February 11, 2027 Key West Theater, 512 Eaton Street Who's Bad brings its Michael Jackson tribute to the Key West Theater. The group has been at this since 2003 and has logged more than 2,500 performances — theaters, clubs, festivals, and House of Blues rooms across the U.S., plus tours through the U.K., China, […] 
February 11 – 13, 2027 Waterfront Playhouse, Mallory Square, 407 Wall Street The Spotlight Series continues with the Florida premiere of Call Me Elizabeth, written and performed by Kayla Boye. It's set on a single morning in May 1961 at the Beverly Hills Hotel, drawn from Elizabeth Taylor's real conversations with the writer Max Lerner […] |
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Featured
Florida Keys Seafood Festival FEBRUARY 13-14, 2027 Two Days of Seafood, Music & Family Fun! Join us for the 20th Annual Florida Keys Seafood Festival at Truman Waterfront Park in Key West. For just $10 admission, enjoy two full days of fresh, local seafood, live music, activities, and the vibrant island atmosphere that make this festival a […] |
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Saturday, February 27, 2027 Doors 6:30pm, Show 7:30pm · Tennessee Williams Theatre Ailey II is the junior company of Alvin Ailey American Dance Theater, and calling it a training ensemble undersells it considerably. Founded in 1974 as the Alvin Ailey Repertory Ensemble, it exists to pair the strongest early-career dancers in the country with choreographers […] |
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March 2 – 20, 2027 · Tuesdays–Saturdays at 7:30pm Red Barn Theatre, 319 Duval Street (rear) The Red Barn stages Bess Wohl's Liberation, winner of the 2026 Pulitzer Prize for Drama and Best Play at the 2026 Tony Awards. Developed by Roundabout Theatre Company, it premiered off-Broadway in February 2025 and transferred to Broadway that […] |
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March 4 – 20, 2027 Waterfront Playhouse, Mallory Square, 407 Wall Street The Waterfront's mainstage series presents Come From Away, the musical by Irene Sankoff and David Hein about what happened in Gander, Newfoundland, on September 11, 2001. When American airspace closed that morning, 38 planes were diverted to Gander's airport, and a town of […] |
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