• 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 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 […]

    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, 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, […]

    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 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, […]

    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. 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 […]

    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 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 […]

  • 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 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 […]

    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 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 […]

    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 2015 and has since played more than 700 shows across 38 states, including a crowd of 18,000 at Kool Deadwood Nights in South Dakota 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 built around traditional and contemporary Irish music. The show is assembled by a creative team based in Ireland and cast with award-winning and World Champion […]

    The Linda Ronstadt Experience

    Key West Theater 512 Eaton Street, Key West, FL

    Friday, March 19, 2027 Key West Theater, 512 Eaton Street The Linda Ronstadt Experience brings its tribute concert to the Key West Theater, fronted by American Idol alum Tristan McIntosh and backed by a full band. The show focuses on Ronstadt at the peak of her career, when she was the biggest-selling female recording artist […]

    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 2001 film, the stage version arrived on Broadway in 2007 with music and lyrics by Laurence O'Keefe and Nell Benjamin and a book by Heather […]