Sail training is a non-formal residential educational experience manifesting in personal and social outcomes, contributing to participant well-being and character formation and development. The origins of modern-day sail training are found in the age of sail's culture and traditions, proposed here as a socio-cultural experience in a vessel-bound cultural community. This paper reports an ethnographic case study of a 117-h sail training voyage as participants, entering this novel and challenging socio-cultural setting, experienced acculturation activating an earlier and more familiar process for social learning, a natural pedagogy for social bonding. The findings are explored further with approaches to informal and non-formal education.