Previous studies have documented higher rates of HIV risk behavior in gay and bisexual men traveling for leisure. Most of these studies collected data in high-risk tourist areas known for promoting alcohol and other substance use. The present study sampled a broader range of men by collecting data at a Gay Pride celebration, and asking participants about vacation experiences over the past 12 months. We also collected information about men's use of the Internet to find sexual partners before they traveled. Overall, two-thirds of participants reported recreational travel in the previous year. Of these men, 17% reported having sex with a new partner during their most recent vacation. Forty-three percent of the respondents were sexually active during their vacation. Sexually-active participants reported a mean of 2.01 unprotected anal sex acts during their brief vacation stay (M = 6.2 days). Close to half of the sexually-active men reported having sex with a partner of unknown HIV status. Alcohol and drug use were associated with unprotected sex. Men who used the Internet to set up dates prior to travel reported significantly more sexual partners and were significantly more likely to report having sex with a new partner. Many gay and bisexual men on vacation report behaviors that may place their health at risk, including substance use and unprotected sexual activity. Interventions designed to reduce risk behaviors in this population are needed.