Travel and overseas experiences, particularly those involving some form of outdoor education, are regarded by many young people, parents, university admissions and employers as somehow beneficial to a young person's development. Often, expedition experiences are happening at crucial times in life (the teen years) when metaphysical (rather than empirical) questions dominate. This paper explores the explicit connections that can be made between the current curriculum in the United Kingdom and expeditions on the basis of contributions to personal and social development through values, choices and decisions. In order for such experiences to be of educational value we argue that creating space for students to make mistakes and to explore (in literal and metaphorical terms) is of crucial importance. The paper concludes that expeditions may provide a useful context for personal and social development and, in particular, exploration of values.