• Dracula: A Comedy of Terrors

    Red Barn Theatre 319 Duval Street - Rear, Key West, Florida

    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, […]

    Unnecessary Farce

    Waterfront Playhouse 407 Wall Street, Key West, FL, United States

    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 […]

    The Pirates of Penzance

    Tennessee Williams Theatre 5901 College Road, Key West, FL, United States

    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 […]

    Afrique en Cirque

    Tennessee Williams Theatre 5901 College Road, Key West, FL, United States

    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, […]

    Who’s Bad

    Key West Theater 512 Eaton Street, Key West, FL

    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 […]

    Call Me Elizabeth

    Waterfront Playhouse 407 Wall Street, Key West, FL, United States

    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. […]

    Ailey II

    Tennessee Williams Theatre 5901 College Road, Key West, FL, United States

    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 […]

  • Liberation

    Red Barn Theatre 319 Duval Street - Rear, Key West, Florida

    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 […]

    Come From Away

    Waterfront Playhouse 407 Wall Street, Key West, FL, United States

    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 […]

    Elton Dan & The Rocket Band

    Key West Theater 512 Eaton Street, Key West, FL

    Saturday, March 13, 2027 Key West Theater, 512 Eaton Street Elton Dan & The Rocket Band bring their Elton John tribute to the Key West Theater. The band formed in […]

    Celtic Angels Ireland

    Tennessee Williams Theatre 5901 College Road, Key West, FL, United States

    Tuesday, March 16, 2027 Doors 6:30pm, Show 7:30pm · Tennessee Williams Theatre Celtic Angels Ireland arrives in Key West on the eve of St. Patrick's Day with a full-scale production […]