Young women in Jamaica face significant risk for HIV and other STIs. A clearer understanding of the factors associated with sexual experience and unprotected intercourse is needed. Data were collected from 330 adolescent females aged 13 to 17 recruited through community based organizations in Kingston, Jamaica, from 2009-2011. Nearly one-third of sexually experienced participants reported not using a condom the last time they had sex. Characteristics associated with sexual experience included older age, marijuana use, and less comfort talking to mother about sexual topics. Characteristics associated with condom use included perceived importance of religion, positive attitudes toward condoms, and not-having multiple sexual partners. Sexually experienced Jamaican female adolescents were engaging in behaviors that made them vulnerable to HIV and other STIs. Interventions with young adolescent girls and their mothers are recommended to postpone sexual debut and promote safer sexual behaviors in those who do engage in sex.