Popular culture and travel are both major points of interest within the realm of leisure in contemporary consumer society. Respectively, they are both highly contentious and diverse fields. This paper explores the more specific areas of popular culture celebrities and alternative tourism in an effort to examine the influence that popular culture and travel engagements have on a segment of Generation Y (Gen-Y) – the gappers. These two areas of leisure activity shape social and cultural norms and influence the construction of self-identity amongst this generation. The aim of this exploratory research is to highlight some areas where popular culture and alternative tourism can be valued as constructive factors influencing a Gen-Y group. The theory of planned behaviour acted as a framework and was used to identify the influence that popular culture celebrity 'Bear' Grylls and his TV show Man vs. Wild had on the alternative tourism engagements of the Gen-Y gappers.