Choosing a specialty school involves huge challenges for families. This research aims to understand the behavioral process that leads families to choose among various specialty school programs. Discrete choice models, based on revealed preferences data from middle school applications in a large school district in Florida, are estimated using both, the top and all-ranked alternatives. This study returns insights into geographic settings, theme specialties and socioeconomic characteristics of applicants, schools and their relationships. Distance from home, the school's academic quality, the school's theme specialty, and the high percentage of applicant's own race are found to be the strongest factors related to the decision to apply.