Journey-based outdoor leaders can be at risk of nutrient deficiencies due to repetitive menus and/or poor dietary practices, with implications for resultant personal health and work performance. Careful meal planning and nutritional understanding can help alleviate this risk. However, overall intakes are also partly dependent on the dietary practices and preferences of outdoor leaders in the field as well as during their days off. This study identifies factors influencing the dietary practices of outdoor leaders from an Australian outdoor education provider and the resultant strategies they implement to manage their diets. Focus groups explored dietary preferences and motivations for dietary practices, with findings corroborated by field observations on two journey-based programs. Inductive thematic analysis identified three key themes influencing the dietary practices of outdoor leaders: food limitations, personal preferences, and social context.