This study focuses on understanding the experiential meaning for participants engaged in events at the nexus of tourism, sport and charity. Using the Constant Comparison Method (CCM), we analyze the published findings of an autoethnographic study on philanthropic adventure tourism with focus group (n = 31) and interview (n = 32) studies of charity sport event participants. Several themes related to the tourism, sport and charitable aspects of the experience are highlighted. Notably, the central role of connectedness is revealed, and the multiple levels for participant connectedness, including with the self, with others and with a greater social cause, and the processes facilitating these connections are discussed. The results extend research on charity sport events to multi-day touring events, while uncovering initial evidence of how these events may facilitate pathways to wellbeing. In addition, implications for autoethnographic research in tourism, and managing experiential meanings within this growing event sector, are highlighted.