The objectives of many outdoor education (OE) programmes are not only to foster the development of intrapersonal, interpersonal and life skills, but also to promote ecological lifestyles, connect communities and influence adult pro-social and environmental behaviour. Failure to do so arguably places our youth at risk of disconnect, from self, others and the natural environment. The Fish River Journey is a compulsory, 21-day, OE programme which includes hiking, running, cycling, kayaking, abseiling, camping and fulfilling a community service curriculum, which has been developed for adolescents attending two independent boarding schools in South Africa. Little is known of the long-term, lasting, effects of this ‘Journey’ or the extent to which this experience affects participants personally, professionally and ecologically. Thus, adopting an underlying social constructivist framework, drawing on the sense of coherence theory (i.e. comprehensibility, manageability and meaningfulness), this research sought to understand whether participants felt that this learning experience in natural spaces had any impact on their current lives. Employing a retrospective approach, this mixed-method study collected online survey material from 2005 to 2020 alumni (N = 224). Quantitative survey findings indicate that, overall, the adventure experience (which included calculated risks) had a positive effect on participants, particularly in terms of appreciating and finding solace in the Eastern Cape biosphere, and improving human connection. Qualitative analysis from semistructured interviews (N = 12) suggests that incorporating the African ethic of Ukama in terms of Understanding, Kinship, Ability, Meaning and Appreciation, could promote improved interconnectedness with self, others and nature.