Sexual risk behavior is higher when people vacation as compared to when they are at home. The current study uses survey data to compare sexual risk behavior of gay men who vacation at gay resorts to those who do not. Independent predictors of vacationing at gay resorts included income level, relationship status, ever having attended a circuit party, and HIV serostatus. For men who visit resorts to meet sex partners, independent predictors included relationship status, ever having attended a circuit party, HIV serostatus, number of male sex partners in the past six months, and number of anal insertive male partners using a condom. These results show a need for the development of structural interventions in the gay resort and hotel setting.