Drawing on cumulative prospect theory (CPT), we measured the risk and motivational factors involved in “canal boat tours” and used these to test conceptual models to predict canal boat tour participant’s behavioural intentions in France. Data were collected using face-to-face questionnaire surveys and subjected to rigorous analysis. In-depth interviews provided deeper insight into participants’ post-purchase behaviour. Assessment of the study results using two key features of CPT – diminishing sensitivity and risk aversion – confirmed that this theory can explain how risk and motivational factors interact to drive canal boat tour participants’ post-purchase behaviours.