The Caribbean has always been viewed as a tourist attraction for pleasure seeking individuals. Over several years, there has been evolved a rather intimate and interactive relationship between visitors and their hosts. The culmination of which is the rather romantic fascination of tourists toward locals in many Caribbean destinations. This is not a new phenomenon, as this pattern is one that evolved at the advent of tourism in the region. Economic and social factors are some of the competing contributors to this phenomenon.It would appear that with the increased influx of tourists in Caribbean destinations, that an astronomical increase in the reported cases of HIV/AIDS and other sexually related transmitted diseases are also witnessed. Trinidad and Tobago (T&T) is amongst the worst exposed in the Caribbean outside of the Dominican Republic and Haiti. Latest reports by the UNAIDS indicates that the number of reported cases in T&T has reached unprecedented levels (over 20,000 in 2009) and continues to increase. This study looks critically at the extent to which tourism and other related leisure activities including carnival, and the cultural diffusion it brings may be contributing to this epidemic. It is also hoped that this study will try to articulate possible suggestions to contain what is increasingly leading to a myriad of cultural, social and economic challenges for the country.