The main objectives of this study were to examine relationships between vacation sex expectations and travelling companionship type (solo, paired, or group), and behavioural outcomes such as engaging in a relationship while on vacation, procuring condoms, and initiating condom use with vacation sex partners among tourist women in Costa Rica. A brief interview was used to assess sociodemographic characteristics, vacation sex expectations and relationships, casual sex variables, and alcohol use among a convenience sample of 128 single female tourists 18 years of age or older. Univariate and multivariate analysis were used to examine relationships among variables of interest. Women who travelled solo or with a single female companion and women who anticipated having sex on holiday were more likely than other tourist women to report one or more vacation relationships, to have procured condoms, and to have initiated condom use with a vacation sex partner. Women who engage in unanticipated vacation relationships may be at increased risk of participating in unsafe sex with a partner met on holiday due to lack of condom procurement and/or initiation of condom use. The findings point to the importance of public health efforts to educate women regarding safer sex precautions when travelling on holiday.