Each year large numbers of Western men travel to Thailand for sex tourism. Although many will use condoms during their sexual encounters, others will not, potentially exposing themselves to the risk of acquiring sexually transmitted infections, including HIV. Although sex tourism in Thailand has been well documented, the social drivers underpinning voluntary sexual risk-taking through the avoidance of condoms remain poorly understood. Engaging with R.W. Connell’s concept of hegemonic masculinity and drawing on data collected from 1237 online discussion board posts and 14 face-to-face interviews, this study considers the ways in which understandings and performances of masculinities may inform the sexual risk-taking behaviours of Western male sex tourists. It argues that for some of these men, unprotected sex is viewed not as a reckless behaviour but, instead, as a safe and appropriate masculine practice, supported by relationships that are often framed as romantic and within a setting where HIV is still largely considered a homosexual disease. With sex workers often disempowered to request safer sexual practices, and some men’s attitudes towards unprotected sex resistant to external health promotion advice, the paper concludes by considering what this might mean for policy and practice.