Flying Lessons

Book by Donald Rupe; Music by Donald Rupe and Cesar de la Rosa; Orchestrations by Cesar de la Rosa, Josh Ceballos and Jason Bailey

In this charming musical, Isabella is a young Latina whose teacher has just assigned the final project of her eighth-grade year: research a historical figure and write a paper about what made them great. Joined by her quirky friends, Isabella has to decide who to study when she is visited in a dream by two unlikely companions: Amelia Earhart and Frederick Douglass. Over time, Isabella writes her own 'recipe for greatness' as she learns as much about herself as she does about history.

Donald Rupe

Donald Rupe (Writer (Book, Music, Lyrics))

DONALD RUPE (Book/Music/Lyrics/Director) is an Orlando-based producer, director, and writer. Currently, Donald is the Director of Theatre at Central Florida Community Arts, an impressive organization that provides performance opportunities in many disciplines for people of all ages ( In his current role, Donald produces a full season of award-winning productions in a converted Blackbox Theatre space in the heart of Downtown Orlando. Donald is also an Adjunct Professor of Theatre at Valencia College and in another life he was a high school theatre teacher for 7 years. Donald began writing at the Orlando International Fringe Festival, where he has enjoyed several successes: From Here (2019, Winner-4 Watermark Splash Awards), Once I Laughed (2015, Winner-Best Musical, Patron's Pick and endorsed by the estate of the Andrews Sisters), among others. Donald (with collaborator Cesar de la Rosa) wrote the first incarnation of Flying Lessons as a result of a grant to bring a theatrical production to the eighth grade students of Osceola County, Florida. Donald received his Master's Degree in Applied Theatre from New York University and his BA in Theatre from Florida State University.

Cesar de la Rosa

Cesar de la Rosa (Music/Orchestrations)

CESAR DE LA ROSA (Music/Lyrics/Orchestrations) is a producer, singer-songwriter and seasoned entertainer. Hailing from the enchanted island of Puerto Rico, Cesar grew up surrounded by his large, musical family. Performing from the young age of 8, Cesar came to Florida to study vocal performance, choir, drama, and dance. In Orlando, Cesar collaborated with some of the world’s leading entertainment companies, including Walt Disney World and Universal Studios. He has also released a debut studio album, toured Europe, Japan, and America, and has been involved in songwriting projects for companies such as Telemundo and MTV. Cesar has since created Push-Love, a production company, in Orlando, Florida.

Joshua Ceballos

Joshua Ceballos (Musical Director/Orchestrations)

JOSH CEBALLOS (Music Director/Orchestrator/Additional Music) was born to Cuban/Dominican parents in Miami, FL and has since found a home in Orlando. Josh is active as a music director, vocal coach, arranger, orchestrator, keyboardist, and pianist. He currently serves as a Staff Accompanist and Music Specialist at the University of Central Florida. He has most recently music directed at the Orlando Shakes (In the Heights), Garden Theatre (Addams Family, Flashdance), Theater at St. Luke’s (Peter and the Starcatcher), and served as the Music Specialist/Pianist for TheatreUCF’s production of Bernarda Alba. He has traveled abroad to the Czech Republic as part of the Prague Piano Festival hosted by Cincinnati Conservatory of Music. Josh stays busy playing keyboards for Violectric, an electrifying band recently seen in Las Vegas. He can also be seen music directing cabarets, arranging music, recording in his home studio, and performing throughout the country.

Jason Bailey

Jason Bailey (Orchestrations)

JASON M. BAILEY (Orchestrations) is a Performer/Pianist/Music Director/Vocal Coach in Orlando. He is currently a staff accompanist for the Theatre department at University of Central Florida where he is also working on his M.A in Musical Theatre with an Emphasis on Music Directing. Jason is a also a vocal coach, currently working on his Estill certification, and teaches privately as well working with schools and theaters in Central Florida. Jason is a Musical Director for many companies including Central Florida Community Arts, Osceola Arts, Rollins College, and UCF and he was recently named one of the top 5 Music Directors in Orlando by the Orlando Sentinel. Jason is also an arts educator, having taught band, choir, and musical theatre for a number of public and private schools as well for nationally acclaimed theaters such as Missoula Children's Theatre, Oregon Children's Theatre, Central Florida Community Arts, and Orlando Repertory Theatre. He began his career as performer and has sung and acted with theatre's across the country including Rocky Mountain Repertory Theatre, Chanhassen Dinner Theatre, American Family Theatre, and Salem Repertory Theatre.