The Florida Studio Theatre 2026 2027 season brings another lively lineup of plays, musicals, comedy and cabaret to Sarasota.
From a Tony Award-winning musical and Teddy Roosevelt to AI, yacht rock and Sarasota traffic circles, FST’s new season has a little bit of everything
Florida Studio Theatre is not exactly easing quietly into its 2026–27 Winter Season.
Instead, Sarasota’s downtown theatrical mainstay is serving up a season that jumps from a Tony Award-winning Broadway musical to Theodore Roosevelt, takes a potentially dangerous detour into artificial intelligence, sails straight into yacht rock and eventually lands—where else?—in a Sarasota traffic circle.
In other words, there should be very little chance of getting bored.
FST’s newly announced Winter Season features four Mainstage productions and three Cabaret shows, mixing Broadway favorites with newer works and original musical revues. Under the theme “Stories That Connect Us: Finding the Light Together,” the season explores relationships, resilience and the wonderfully complicated business of being human.
And sometimes, apparently, being human means knowing when to keep AI out of your marriage.
A Broadway Favorite Starts Things Off
The Mainstage Series opens November 18, 2026, at the Gompertz Theatre with Kimberly Akimbo, the acclaimed musical with book and lyrics by David Lindsay-Abaire and music by Jeanine Tesori.
Winner of the Tony Award for Best Musical, Kimberly Akimbo centers on a teenage girl dealing with some decidedly non-typical growing pains. Beneath its quirky humor is a story about family, time and making something meaningful out of the life you have.
It is funny, touching and wonderfully unconventional—the sort of musical that manages to make audiences laugh while quietly sneaking up on their hearts.
Teddy Roosevelt Returns to Sarasota
Beginning December 9 at the Keating Theatre, FST brings back The Bully Pulpit by Michael O. Smith.
The acclaimed one-man play places Theodore Roosevelt front and center as he revisits the triumphs, tragedies and defining experiences that shaped his extraordinary life.
From personal heartbreak to the presidency, Roosevelt’s story unfolds as something far more intimate than a history lesson.
The production originally premiered at FST in 2004, making its return something of a homecoming—and considering Roosevelt was never exactly known for being a shrinking violet, expect plenty of personality.
When AI Becomes the Third Wheel
Then things get extremely 2027.
Upgrade by Sandy Rustin begins February 3 in the Gompertz Theatre as part of its world premiere.
After appearing in FST’s 2026 Burdick New Play Reading Festival, the comedy moves to the Mainstage with a premise that feels almost suspiciously timely: What happens when artificial intelligence gets a little too involved in an Upper West Side couple’s marriage?
Yes, apparently there are now three people in this relationship—and one of them may know entirely too much.
Upgrade plays with love, technology, marriage and our endless desire to improve things that perhaps did not need quite so much improving in the first place.
Funny? Certainly. Slightly unnerving considering how quickly AI is finding its way into everyday life? Absolutely.
And that may be precisely the point.
Letting the Light In
The Mainstage season concludes beginning April 7 with How the Light Gets In by E.M. Lewis, playwright of the FST favorite Dorothy’s Dictionary.
This time Lewis brings together four very different lives that become unexpectedly intertwined.
The characters arrive carrying their own struggles, but gradually discover possibilities for connection, healing and hope.
After the laughs, technology and larger-than-life personalities elsewhere in the season, How the Light Gets In promises something quieter and deeply human—a fitting conclusion to a season built around connection.
Now, About That Yacht Rock…
Over in the Cabaret, FST is loosening its collar considerably.
The Winter Cabaret Series launches September 23, 2026, with Sailing: Yacht Rock and Beyond in the Court Cabaret.
Think smooth harmonies, breezy melodies and the gloriously laid-back sounds of the 1970s and ’80s.
Songs including “Sailing,” “Margaritaville” and “Brandy” help set the mood.
Frankly, Sarasota and yacht rock seem destined for each other. All that is missing is a sunset, a boat drink and someone asking where you parked the Bentley.
American Music With Something to Say
Beginning November 4 in the Goldstein Cabaret, American Rebels celebrates America’s 250th anniversary through artists and songs that challenged conventions, inspired generations and helped define American culture.
From “Born in the U.S.A.” to “Man in the Mirror,” the revue looks at musicians who did more than entertain. They questioned, provoked and sometimes changed the conversation.
That makes American Rebels less of a nostalgic jukebox ride and more of a musical look at the voices that helped shape the country.
And Then Sarasota Gets Roasted
Finally, FST saves some of its sharpest ammunition for Laughing Matters: Volume 7, opening February 10, 2027, in the Court Cabaret.
Nothing, it seems, is safe.
Artificial intelligence? Fair game.
Weight-loss shots? Absolutely.
Pickleball? Of course.
Traffic circles?
Now it’s personal.
The fast-paced comedy revue takes aim at today’s trends along with the peculiarities of everyday life on the Suncoast.
And anyone who has attempted to navigate a Sarasota roundabout with a driver who suddenly decides traffic laws are merely suggestions knows there is plenty of material.
Seven Shows, One Very Sarasota Season
What makes FST’s 2026–27 lineup particularly interesting is just how different these seven productions are.
There is Broadway polish and intimate drama. History gets its moment, but so does artificial intelligence. There are songs that defined generations, breezy yacht-rock favorites and enough contemporary absurdity to keep Laughing Matters supplied with punchlines.
Yet running underneath all of it is the idea FST has chosen for the season: connection.
Sometimes we find it through music. Sometimes through laughter. Sometimes through another person.
And apparently, sometimes while desperately trying to determine who has the right of way in a traffic circle.
Florida Studio Theatre is located at 1241 N. Palm Ave. in downtown Sarasota. For performance schedules, subscriptions and ticket information, visit Florida Studio Theatre’s official website or contact the FST Box Office at 941-366-9000.
https://www.floridastudiotheatre.org
