Key West's Theatrical Extravaganza: A Season of Laughs, Tears, and Showstoppers

Key West is transforming into a thespian's paradise this season, unleashing a cavalcade of musicals, comedies, dramas, and all things theater. Let’s spotlight some of these stage sensations.

First up, we’ve got the Red Barn Theatre, an 1829 vintage charmer at 319 Duval St. This season, they’re serving up "POTUS: Or, Behind Every Great Dumbass Are Seven Women Trying to Keep Him Alive," a presidential farce running Jan. 30 – Feb. 24. Don't miss the "woke" satire "The Thanksgiving Play" (March 5-30) and "The Lifespan of a Fact" (April 9 – May 4), a drama teetering between truth and fiction. Showtime’s 8 p.m., folks! Head over to for more.

Splashy and classic, the Waterfront Playhouse at 310 Wall St. is next. They’re bringing "Singin' in the Rain" (Jan. 24 – Feb. 17) to life, complete with iconic tunes like “Make ’Em Laugh.” Agatha Christie’s "Murder on the Orient Express" (March 13 – April 6) promises mystery, while Tennessee Williams’ birth is celebrated with "Ten Blocks on the Camino Real" (March 17). Mix in some "Trunk Material" (March 31) and Neil Simon’s “Lost in Yonkers” (April 24 – May 11), and you’ve got a recipe for unforgettable nights. Check out for details.

Fringe Theater Key West, the cradle of art-house magic at 600 White St., is dishing out "Key West Characters True Stories" (Feb. 22-23), a tapestry of plays and music. They’re also staging "The Last Five Years" (March 13-23) and "Death and the Maiden" (April 17-27). Head over to for tickets to these intimate performances.

Over at 5901 College Road, the Tennessee Williams Theatre is not just about shows; it’s a community cornerstone. This season's must-sees include "Little Women, the Broadway Musical" (March 5), "Neil Berg's 50 Years of Rock n' Roll, Part IV" (March 20), and "Dinosaur World, Live!" (April 2). Ballet fans, mark April 25 for "Ballets Trockadero de Monte Carlo.” Visit for the full lineup.

The Key West Theater at 512 Eaton St. is your go-to for a medley of performances. Tom Papa tickles your funny bone on Feb. 3-4, while "Kathy Gilmore and Friends” stir up laughs on Feb. 26. Scoot over to for a full rundown.

Comedy Key West at 218 Whitehead St., Unit 5, is where the stand-up scene is at. February’s lineup includes Kerryn Feehan, Shane Mauss, and a parade of laugh masters. Derrick Stroup and Joe Matarese light up March, while April kicks off with Amos Gill. Swing by for a giggle or two.

Last but not least, The Studios of Key West at 533 Eaton St. is the heartbeat of local creativity. It’s a whirlwind of performances, workshops, and exhibitions. “First Look" readings, dance narratives, and monologues on service industry woes are just a teaser of their offerings. Get the full artistic scoop at

So, Key West is definitely the place to be for theater buffs this season. Break a leg, folks!