Curtain Rises on Florida Keys Theater Season

FLORIDA KEYS — The 2025 performing arts season in the Florida Keys & Key West is set to captivate audiences with lively musicals, comedies, dramas and other top-notch performances. Here are some upcoming highlights.

Since 1978, The Key Players group has brought live community theater to the Upper Keys. The next production, “Almost, Maine,” is scheduled to run Feb. 27 through March 9. The romantic comedy is written by John Cariani and features nine short plays that explore the themes of love and loss in a remote “town” called Almost, Maine. Performances take place at the Murray E. Nelson Government & Cultural Center, located at 102050 Overseas Highway in Key Largo. For tickets and more information, visit thekeyplayers.org or call 305-942-4339.

Founded as a small community group in 1944, the Marathon Community Theatre, located at 5101 Overseas Highway, has grown into a vibrant hub for memorable and popular performances by talented local residents. Productions include Jones Hope Wooten's comedy "Always a Bridesmaid," concluding its winter run Feb. 6-8 with an 8 p.m. curtain. The show "Nunsense" is to run from March 13 through April 12 at 8 p.m., with a March 30 matinee at 3 p.m. This musical comedy follows five nuns from The Little Sisters of Hoboken as they stage a talent show to raise money to bury their sisters, who tragically died from botulism after eating tainted soup. For more information, visit marathontheater.org or call 305-743-0994.

Originally built in 1829 as a carriage house, Key West’s Red Barn Theatre at 319 Duval St., rear, has hosted modern-era performances since 1981. This season’s lineup features “Ms. Holmes and Ms. Watson, Apt. 2B” (through Feb. 22), a darkly comic, feminist reimagining of Sherlock Holmes and Dr. Watson; “Brooklyn Laundry” (March 4-29), John Patrick Shanley’s poignant and funny exploration of three sisters and a Brooklyn laundry owner; and “Short Attention Span Theatre: Alternative Facts” (April 8 through May 3), an audience favorite showcasing eclectic short plays with surprising twists. For tickets and details, visit redbarntheatre.com or call 305-296-9911.

Entertaining audiences for over 80 years at its 310 Wall St. location near Key West’s Mallory Square, the Waterfront Playhouse presents the Florida premiere of the newly published farce “The Angel Next Door” through Feb. 8. Capturing the joy, sophistication and wit of 1940s screwball comedies, the production sets the stage for an exciting spring lineup, including the classic musical “La Cage Aux Folles” (Feb. 26 through March 22), the one-man show “A Distant Country Called Youth” celebrating Tennessee Williams (March 27–29), and Frederick Knott’s suspense drama “Wait Until Dark” (April 16 through May 3). For tickets and details, visit waterfrontplayhouse.org or call 305-294-5015.

Fringe Theater Key West, dedicated to art-house productions in intimate settings, will stage most of the season’s performances at The Armory, 600 White St. The lineup features “Goodnight Oscar” running Feb. 18 through March 1, a darkly comic drama about actor and composer Oscar Levant's genius, mental health struggles and unforgettable 1958 Tonight Show appearance. The schedule also includes “Kaleidoscope,” set for March 12-14 and celebrating pianist Michael D. Robinson and his chromesthesia (a sound-to-color perceptual phenomenon). “More Key West Characters,” running April 23-24, is a community project with Key West’s Williams Hall that showcases true local stories. For tickets, visit fringetheater.org or call KeysTix at 305-295-7676.

The Tennessee Williams Theatre, at 5901 College Road on the campus of the College of the Florida Keys, is a nonprofit venue showcasing Broadway national tours, performing artists and theatrical experiences. Highlights this season include “A Blonde, Brunette, & Some Duets,” scheduled Feb. 8 and featuring Eric McCormack and Laura Bell Bundy in an unforgettable evening of Broadway hits, cinematic charm and chart-topping tunes. "Joy Hawkins in the Cabaret" is set for March 12-13; and “MOMIX: Alice,” inspired by the classic Alice in Wonderland story, is to blend illusion, acrobatics, magic and whimsy March 19. “The Peking Acrobats,” showcasing trick cycling, precision tumbling and gymnastics, are to take the stage March 23. The theater supports the Florida Keys community through its Children’s Outreach Series, which provides accessible live theater experiences for Keys kids. Visit keystix.com/twt or call 305-295-7676 for tickets.

The Key West Theater, a versatile performing arts center at 512 Eaton St., hosts national touring artists, comedy shows, concerts, local songwriter showcases and more. Upcoming comedic performances include Garrison Keillor (Feb. 17), Nick Swardson (Feb. 20), Kevin Nealon (March 2) and the hilarious "Golden Girls: The Tribute Show — A Drag Parody" (March 16). Visit thekeywesttheater.com for a full calendar of upcoming shows and tickets.

Comedy Key West, located at 218 Whitehead St., Unit 5, showcases top-notch local and visiting stand-up comedians including Comedy Central stars and nationally recognized performers. February highlights include Doug Stanhope (Feb. 1), Matt Bergman (Feb. 3-5), Dave Smith (Feb. 6-8), “Hemingway in a Funny Way” (Feb. 7, 14, 21 and 28), the “Brothers from Another Mother Comedy Tour” (Feb. 10-12), Dave Landau (Feb. 13-16), a special Comedy Music Jam (Feb. 17), the MadHouse Open Mic (Feb. 18), Louis C.K. (Feb. 20-22), Ross Bennett (Feb. 23-25) and Mary Mack (Feb. 26 through March 1). March features Kurt Metzger (March 2-4), Dwayne Perkins (March 5-8), “Hemingway in a Funny Way” (March 7, 14, 21 and 28), Chad Daniels (March 9-11), John Caparulo (March 13-16), Comedy Music Jam (March 17), the MadHouse Open Mic (March 18 and 25) and Patrick Garrity (March 26-29). April brings Jim Norton (April 18-19) and “Hemingway in a Funny Way” (April 4, 11 and 25). For tickets and information, visit comedykeywest.com or call 305-985-7370.

The Studios of Key West supports artists, inspires creativity and builds community. Located at 533 Eaton St., the facility hosts performances, workshops, concerts and exhibitions while also featuring local studios and an artist residency program. February highlights include "Write Me a Romance," a romantic comedy by award-winning author and television producer Hy Conrad (through Feb. 1); "Microparty," a unique performance blending acting, live music, puppetry and dance (Feb. 14-16); and "The Myth of the Two Marcos" by Tony Meneses (Feb. 20 and 22). March offerings include "Journey of the Two Spirit: Table Read and Conversation with Moriah Joy" (March 7), which explores finding one’s voice through art and transforming marginalization into power; "Swimming in the Dark," an opera about choice and political freedom (March 21–22); and Carey Perloff’s "Vienna, Vienna, Vienna" (March 28-29), a poignant play about forgiveness and survivor guilt. Visit tskw.org or call 305-296-0458.