Journeys and expeditions are an important practice in outdoor and environmental education which often get overlooked or may be under-valued. The benefits of journeys and expeditions are considerable and an understanding of their historical development is helpful in gaining insights into current outdoor practices in a multitude of contexts and cultures. This chapter begins by reviewing a few iconic explorers and their journeys and expeditions, highlighting the broad use of the terms and a range of different purposes before examining the benefits and the learning processes involved (primarily focusing on young people and youth development). Research points clearly to the benefits across multiple domains and over extended periods of time. Studies draw on Philosophy, Psychology, Education and Sociology and indicate consistent and considerable contributions to moral development, spiritual growth, environmental stewardship, personal and social development alongside GRIT and resilience. Challenges for planning, executing and managing journeys and expeditions are discussed, these include: time; cost; environmental impact and expedition reverse culture shock, which can all contribute to making the justification for incorporating journeys and/or expeditions into educational curricula all the more difficult. It is important that those working in this area are aware of these challenges and learn to manage them appropriately in order to gain optimum benefit from these powerful outdoor learning tools.