This study tested an empirical model of the relationship between Personal Positive Youth Development (PPYD) and two contextual factors: Positive Parenting (PP), and Perception of the Climate and Functioning of the School (PcfS). The hypothesis tested was that a positive relationship with parents and a positive perception of the school will contribute to the prediction of PPYD. The sample was composed of 1507 adolescents recruited in 10 Spanish schools who were aged between 12 and 18 years and 52% were female. PPYD was evaluated through Dispositional optimism, Self-competence, and Sense of coherence. PP was evaluated through Affect and communication, Autonomy granting, Humor, and Self-disclosure. PcfS was evaluated through School climate, School bonds, Clarity of rules and values, and Empowerment. Previous reliability and validity analyses of the constructs were carried out, and correlational analyses and structural predictions were made. The results show that both PP and PcfS were associated with better scores in PPYD. Also, a positive correlation between those two contextual factors was found. Implications for applied research are discussed.