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    • Poster for 'Call Me Elizabeth' at Waterfront Playhouse Key West, featuring a woman in profile by a window and the dates February 11–13, 2027.

    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. […]

    shrimp on plates
    Featured

    Florida Keys Seafood Festival

    Truman Waterfront Park Key West, FL, United States

    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 […]

    Dancer in a gold costume leaps mid-air over a line of fellow performers on a dark stage.

    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 […]

    • Book cover for Liberation by Bess Wohl, with 'Tony Award & Pulitzer Prize Winner' above and colorful rainbow stripes across the title.

    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 […]

    Poster for Come From Away: bold yellow title on a blue airplane-grid background with the Waterfront Playhouse logo and dates March 4–20, 2027.

    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 […]

    A man in a blue hat and patterned shirt plays a grand piano on a dimly lit stage, candlelight illuminating the scene.

    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 […]

    Poster for 'The Linda Ronstadt Experience' featuring American Idol star Tristan McIntosh.

    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 […]

    Promotional poster for Legally Blonde the Musical with a performer in a pink dress and a small dog on a purple background.

    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 […]

    • Taste of Key West

    Truman Waterfront Park Key West, FL, United States

    Taste of Key West Monday, April 5, 2027 · 6:00–9:00 PM · Truman Waterfront Park Key West's Premier Food & Wine Festival Key West's biggest food and wine night takes […]

    Poster for Waterfront Playhouse's Dial M for Murder — red background with large white text, a telephone graphic, and dates April 8–17, 2027.

    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 […]

    Seven-member band lineup posing in a dim, brick-walled venue; six men and one woman, the woman in red, all in dark clothing.

    10,000 Maniacs

    Key West Theater 512 Eaton Street, Key West, FL

    Sunday, April 11, 2027 Key West Theater, 512 Eaton Street 10,000 Maniacs play the Key West Theater. The band formed in Jamestown, New York in 1981 and has sold more […]