This article focuses on transitioning from boys to men -- the possibilities of "becoming-man" -- through outdoor education programs, while acknowledging that a similar investigation could be carried out in relation to girls and women, as well as other gender identities. In relation to becoming-man, contact with nature through an expedition inherently offers some possibilities for confronting one's own boundaries, overcoming pain and suffering, experiencing unsafe situations, being self-sufficient, and belonging to a social group. Several days in a natural environment without the trappings of civilization serve as a developmental instrument for "becoming-man". In approaching this focus I have drawn on phenomenological philosophy because it can open pathways to understanding different ways of being and becoming. Differences in the experiences of men and women (and not excluding other gender identities), when explored phenomenologically, are perceived not only from the position of socially constructed gender, nor from the position of biologism, but from ways of being men and ways of being women, including their different bodily groundings. This perspective suggests that there are needs which adolescent boys have which differ from those of adolescent girls.