Adolescents exhibit significantly lower sun protection behaviours than adults in Australia. While many studies have assessed the sun protection behaviours of adolescents during summer, few studies have explored the differences in sun protection behaviours of adolescents across key contexts relevant to adolescents during summer—notably school time, weekends and school holidays. Greater understanding of differences in behaviours across these contexts provides more detailed explanations of the nature of adolescent ultraviolet exposure and thereby facilitates improved targeting of interventions for this segment whose behaviour is considered hard to change. In this study, we explore the differences in self-reported, habitual, sun protection behaviours of adolescents across key contexts during summer. A sample of 692 adolescents aged between 12 and 18 completed a self-report survey concerning habitual sun-related behaviours across four key contexts. Comparisons were made between contexts in seven key sun protection behaviours. The results show that there are significant differences in habitual sun protection behaviours of adolescents between contexts and notably increased compliance with sun protection behaviours in the school context. These findings suggest that some sun protection behaviours are not transferred between key contexts relevant to adolescents and highlight an opportunity for public health programmes to focus more specifically on facilitating the transfer of positive sun protection behaviours between contexts.