School nurses are well positioned to address risk-taking behaviors for adolescents in their care. The purpose of this mixed-method exploratory study was to explore risk taking in Afro-Caribbean adolescents in South Florida, comparing first- to second-generation adolescents. Quantitative and qualitative data were collected from an immigrant group using the adolescent risk-taking instrument to evaluate risk-taking attitudes, behaviors, and self-described riskiest activities. One-hundred and six adolescents participated; 44% were first generation Afro-Caribbean. Data analysis included analysis of variance, frequencies, and content analysis. There were no differences in risk-taking attitudes; smaller percentages of first generation Afro-Caribbean adolescents reported sexual activity, substance use, and violence. Over one third of the sample, regardless of generational status, reported alcohol use, but did not note alcohol or other health-compromising behaviors as "riskiest" activities. It is important to better understand Afro-Caribbean adolescents’ perspectives about risky behaviors, and school-based venues offer the best promise for reaching these adolescents.