This paper describes the process and findings of a multinational study of the characteristics of sail training for young people. The study used a structured qualitative method and involved "indigenous practitioner-researchers" who collected the majority of the data. Our findings show that participation provides an opportunity for learning in the practical and cognitive domains in relation to skills and knowledge, and in the affective domain in relation to social confidence. The data collected provide evidence that sail training has positive benefits in terms of participants' social confidence and their self-perceptions of capacity to work collaboratively with others. It is argued that while sail training experiences are generally positive and beneficial, some appear to be more effective than others in developing social confidence. We also show that it is not principally the seamanship dimension of the experience, but the combination of a structured purposeful programme with the unique character of the seafaring environment that provides the basis for that learning. The more effective experiences in this respect appear to be those where there is a greater emphasis on specific programme activity. Sail training should therefore be understood not solely as adventurous recreation but as a powerful educative experience.