Adolescents experiment with risk behaviors, including delinquency, substance use, and sexual activity. Multi-level social factors, such as having high-risk peers, neighborhood risks, and parental monitoring, influence adolescents' behaviors. We modeled transition patterns in Bahamian adolescents' risk behaviors across three high school years and examined the effects of multi-level factors. We collected data from 2,564 Bahamian adolescents in Grade 10 and follow-ups through Grade 12. We used latent transition model to identify adolescents' risk statuses. Further analyses used multinomial logistic regression to explore the effects of multi-level factors on assignment to those latent statuses and transitions. We identified four distinct statuses: "low risk" (47.9% of the sample at baseline), "alcohol use" (36.8%), "alcohol use and sexual activity" (5.5%), and "high risk" (9.8%). Males were more likely to be in higher-risk statuses at baseline and to transition from a lower-risk status in Grade 10 to a higher-risk status in Grade 11. Social risk factors were significantly associated with higher-risk statuses at baseline. Neighborhood risk and peer risk involvement continued to affect transitions from lower to higher risk; parental monitoring did not have a significant effect in later years. Our findings have important implications for developing targeted and developmentally appropriate interventions to prevent and reduce risk behaviors among middle-to-late adolescents.