Allison and Von Wald (2010) highlight the substantial opportunities presented by expeditions to address the crucial topic of personal and social development. The present paper wishes to address the apparent oversight of transfer within such learning experiences. Issues that need to be addressed if the impact of transfer is to be optimised are exemplified using four categories, relating to both outcome and process considerations. Furthermore, it is argued that transfer should not be assumed, but rather carefully planned for and attended to as part of any curriculum or development activity. Consequently, facilitation of transfer outcomes by a leader may need to involve both transactional and transformational direction, in addition to consideration of environmental factors and the participants themselves.