Background: Over the last three decades, men's health has emerged as an area of research interest. The relationship between male socialization, the performance of masculinity and health behaviour has been well established. Within the Caribbean, however, there is a gap in the literature on how masculinity affects health beliefs and behaviour. Aim: This study explored men's accounts of "doing" masculinity and the implications for health beliefs and behaviours in order to make recommendations for developing male sensitive health services. Methodology: Men between the ages of 19-60 years in Trinidad and Tobago participated in this study during the period August 2011 to January 2012. Fourteen focus group discussions were conducted among men from various socio-demographic groups and twelve semi structured interviews with men involved in clinical and social programs targeting males. Data were coded thematically using inductive and deductive analysis. Findings: This study is a contribution to the literature on masculinity, in general, and masculinity and health in the Caribbean, in particular. Men reported three core elements for performing masculinity: being a provider, being a leader and being heterosexually promiscuous. However, these expectations could not be realized fully in their personal experiences. Men were expected to take risks and show disregard for their own health and yet perceived being healthy as essential for 'being a man'. Views about prostate cancer screening were an example of this tension: men wanted to be healthy, were positive about screening in principle but unwilling to access services. Implications for policy/practice: Men were willing to talk openly about their health risks, suggesting that they might be willing to access services perceived as sensitive to their needs. Health information and services must be developed and implemented with men in mind to encourage greater participation in health service delivery.