Another unique entertainment option at The Winter Park Playhouse is our Spotlight Cabaret Series in the beautiful lobby piano bar. Different professional singers are featured in this monthly series and the New York-style cabaret performances are approximately 55 minutes in length with no intermission. Tickets for this very popular offering are $20. Students must be 15 years of age or older to be admitted to our cabaret series.  
Tickets for this very popular offering are $20 with a one drink minimum. Advance reservations and early arrival are strongly recommended as seating is limited. Tickets can be purchased online or by visiting or calling the box office at (407) 645-0145. 


Caila Carter

In A Sentimental Mood

The Ultimate Jazz Evening featuring the songs of
Billie Holiday, Sarah Vaughn, Ella Fitzgerald and more!

Live performances at the Playhouse: November 16 & 17, 2022

Virtual encore viewing: December 2–5, 2022

Caila Carter will debut her new solo jazz cabaret In A Sentimental Mood as part of The Winter Park Playhouse Spotlight Cabaret Series on November 16 and 17, 2022. Playhouse Music Director Christopher Leavy will accompany on piano.

Ms. Carter, who has performed several times on the Playhouse Mainstage (A Grand Night For Singing, Crazy For Gershwin, The Florida Festival of New Musicals), will give patrons an evening of quintessential jazz as she pays tribute to legendary artists Billie Holiday, Sarah Vaughn and Ella Fitzgerald as well as modern jazz artists like Cecile McLorin-Salvant.

Caila is a gifted and sought after performing artist whose talents have taken her all over the world. Her resume boasts credits from Hong Kong Disneyland, Norwegian and Oceania Cruise Lines and Universal Studios Orlando. She has a genuine love for all facets of The Arts, and has extensive experience working as both a performing and teaching artist for numerous organizations throughout Central Florida.

"Caila is an incredible singer and we are thrilled to feature her on our cabaret stage! It's going to be a fantastic evening of jazz as she celebrates the great artists of today and yesterday. This cabaret will sell out so get your tickets early!" confirms Heather Alexander, Playhouse Executive Director.

General admission tickets for live cabarets are $20 plus a one drink minimum.

The live cabaret will take place in the theatre lobby bar area. General admission seating is first come first served. Seating is limited and performances sell out quickly, so advance reservations are strongly recommended.


The live cabaret will be filmed and available to enjoy virtually December 2–5. Virtual tickets are $20 and can be purchased by clicking below. The private link and password to view the performance will be sent via email on Friday, December 2nd at 5pm.

If you have any questions regarding this purchase, please call our Box Office at 407-645-0145 and we will be happy to assist you.