Introduction Educational expeditions, particularly overseas youth expeditions, are a growing sector within the broader field of outdoor education (Allison&Von Wald, 2010). The human dimensions of educational expeditions can be complex, challenging, and critical to an expedition's success or failure. Educational expeditions often neglect adequate preparations for the interpersonal challenges while focussing on logistical or physical challenges (Potter, 1997). This paper seeks to explore ways in which interpersonal challenges frequently centre on the tension between individual liberty and social order (Beames&Stonehouse, 2007). Though no formula is likely to address every human dimension of an expedition, expedition leaders and outdoor educators could enhance their expeditions, and potentially illuminate complex interpersonal conflicts, through the introduction of a communitarian philosophical framework.