ABSTRACT Introduction The school‐to‐work transition (STWT) represents the initial significant career milestone in young people's lives. In Italy, the Paths for Transversal Skills and Orientation (PCTOs) were introduced in upper secondary schools as an educational tool to support STWT. PCTOs aim to equip students with transversal skills that promote employability and personal development. Given limited research on PCTO effectiveness, this study examines specific PCTO characteristics in enhancing students' transversal skills and career resources. Methods A cross‐sectional study was conducted between April and May 2024. 567 students (M age = 17.30, SD age = 1.02, 72% males) from two vocational schools (grades 11–13) in central Italy completed a questionnaire assessing four PCTO indicators: orientation value, student involvement in PCTO design, number of PCTO experiences, and quality of the tutor‐student relationship. Transversal skills and career motivational resources were also evaluated. Results A path analysis model revealed positive associations between PCTO indicators and students' transversal skills, which, in turn, were related to career motivational resources. Contrary to expectations, the quality of the tutor–student relationship did not show direct associations with the outcomes. Additionally, results suggested that engaging in various PCTO activities may reduce the clarity of career orientation. Conclusions Findings highlight that a quality PCTO planning fosters transversal skills, indirectly enhancing career resources. While different PCTO experiences support skill development, they may reduce the “orientation” value of the Paths. This study underscores the value of PCTOs in preparing young people for the labor market, emphasizing the importance of targeted, skill‐oriented experiences.