Leslie Beard was director James Kicklighter's second choice for the role, after the first candidate cast for filming dropped due to scheduling conflicts.
Charlotte Czekala was not initially slated for filming, but was selected two weeks into filming in Montepulciano, Italy to provide a grounding for the film. After having a few conversations with director James Kicklighter, one of her life experiences included starting a Drug Abuse Treatment Center, for which she made an appearance on Donahue (1967) in the 1980s.
Director James Kicklighter and Narrator J. Michael Moncrief both grew up in the same hometown of less than 200 people, but neither knew each other until their careers had begun.
Though J. Michael Moncrief plays the role of "Narrator", Director James Kicklighter narrates the story. However, Moncrief did the first recording of the narration. In post-production, it became clear to the producers that it wouldn't make sense for him to serve as the narrator, due to the structure of the film.
Di Passaggio was shot entirely without a crew on-site in Italy for cost purposes. Director James Kicklighter reviewed footage at the end of each day, took notes, and sent them back to the producers in the United States. Utilizing the Internet and a massive outline (taking up four poster boards), each character's story was carefully followed during production. Kicklighter also took two classes for college credit while filming.