Mar 4, 2026 - Mar 21, 2026 Winner of eight Tony Awards, including Best Musical, Once tells the story of a disillusioned Dublin street musician whose music — and life […]
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Mom’s Best Friend By Dan McCabe Directed by Kate Whoriskey Fri Mar 20 & Sat Mar 21, 8pm June and her adult daughter, Christine, talk on the phone […]
Featured
Randy Roberts and Donna McKechnie
The Studios of Key West 533 Eaton St, Key West, FL, United StatesRandy Roberts and Donna McKechnie Spotlight Cabaret curated by Randy Roberts Two showstoppers share one unforgettable stage. Broadway legend Donna McKechnie, Tony® Award winner for A Chorus Line, joins master entertainer […]
My Maria By Andrew Russell Directed by Morgan Green Fri Apr 3 & Sat Apr 4, 8pm A bold and highly theatrical play set in a fictional southern Midwest town, […]
October 15 – 23, 2026 Waterfront Playhouse, Mallory Square, 407 Wall Street The Waterfront Playhouse opens its season with an encore presentation of Hedwig and the Angry Inch, staged as […]
Featured
Key West Fantasy Fest!
October 16 - 25, 2026 2026 Theme: Musical Icons & Iconic Musicals Fantasy Fest is an annual 10-day party in paradise for grown-ups. Started in 1979 by a small group […]
November 12 – 14, 2026 Waterfront Playhouse, Mallory Square, 407 Wall Street The Waterfront Playhouse launches its Spotlight Series with the Florida premiere of , a solo play written by […]
It’s a Wonderful Life: A Live Radio Play
Waterfront Playhouse 407 Wall Street, Key West, FL, United StatesDecember 2 – 17, 2026 Waterfront Playhouse, Mallory Square, 407 Wall Street The Waterfront Playhouse's holiday show turns the theatre into a 1940s radio studio for It's a Wonderful Life: […]
December 8, 2026 – January 2, 2027 · Shows at 7:00pm Red Barn Theatre, 319 Duval Street (rear) The Red Barn opens its holiday slot with Shooting Star, a two-hander […]
January 7 – 9, 2027 Waterfront Playhouse, Mallory Square, 407 Wall Street The Spotlight Series continues with Blanche and Beyond, Steve Lawson's one-man play assembled from Tennessee Williams's own letters. […]
Monday, January 18, 2027 Doors 6:30pm, Show 7:30pm · Tennessee Williams Theatre America's premiere doo wop group brings a brand-new show to the Tennessee Williams Theatre stage this January. The Doo […]
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, […]
