This article presents preliminary findings of a randomized HIV prevention study in Trinidad and Tobago in the Caribbean. The study centers on a family HIV workshop aimed at strengthening parenting skills that are empirically linked to reducing adolescent HIV exposure and other sexual risks. These skills include parental monitoring; educating youth about HIV, sex, and other sexually transmitted infections (STI's); and discussing cultural and interpersonal pressures to have sex. Participants include 180 primary caregivers and their 12--14-year-old adolescents randomized to either the Trinidad and Tobago family HIV Workshop (N = 92) or a general workshop (N = 88). Intervention and control group participants completed pretest and posttest measures on parenting and HIV risk outcomes. Compared to controls, intervention parents reported improvements in HIV knowledge (d = 0.79); attitudes toward AIDS (d = 0.42); general communication with adolescents (d = 0.94); conversations with adolescents about sex (d = 0.95); conversations about sexual risks and values (d = 0.43); monitoring of adolescents (d = 0.34); conflicts with adolescents (d = 0.30); and intensity of daily parenting hassles (d = 0.35). Intervention and control parents did not differ in behavioral control, use of positive parenting techniques, and expansion of support networks. Implications for addressing rising HIV risks among young people in Trinidad and Tobago and the Caribbean are discussed.