Research evidence suggests that outdoor education offers significant potential in priming healthy physical activity behaviors, developing life skills, enhancing self-esteem and promoting improved academic performance. The aim of the current study was to explore from a cross-sectional perspective the perceived benefits of a dinghy sailing program on 9-13-year-old school children. Participants (n = 38) were drawn from a diverse range of relevant participation and stakeholder groups, including school children, teachers and sailing instructors. Semi-structured interviews (adults) and focus groups (children) were used to collect data, with inductive data analysis methods applied. Six superordinate themes arose from the data highlighting physical and mental health benefits as well as the potential to development key life skills, self-esteem and the possible interaction with other aspects of the school curriculum to enhance student learning.