• 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, […]

    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 […]

    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 […]

    Legally Blonde the Musical

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

    Monday, March 29, 2027 Doors 6:30pm, Show 7:30pm · Tennessee Williams Theatre The Broadway national tour of Legally Blonde the Musical stops in Key West this spring. Adapted from the […]

  • Dial M for Murder

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

    April 8 – 17, 2027 Waterfront Playhouse, Mallory Square, 407 Wall Street The Waterfront's mainstage season concludes with Dial M for Murder, Frederick Knott's 1952 thriller in Jeffrey Hatcher's 2022 […]