The purpose of this study was to carry out a preliminary investigation to explore the use of outdoor and adventurous project work (PW) within an educational setting. Specifically, differences between the PW and normal academic school experiences were examined using a self-determination theory framework integrated with a goal orientation and psychological skills perspective. Additionally, an exploratory investigation was carried out to examine the extent to which key motivation constructs predicted skill development (i.e. problem solving, collaboration and communication) through the PW experience. Six questionnaires were adapted and utilised to collect the relevant data for both school and PW experiences (Basic Psychological Needs questionnaire; the Learning Climate Questionnaire; Intrinsic Motivation Inventory; the Motivated Strategies for Learning Questionnaire; 2 x 2 Achievement Goal Questionnaire and perceived skills learned in PW questionnaire) from the 224 students (Mean age 13.2 ± 0.3 years) who participated in the 12-day PW. Results indicated that there were significant differences between school and PW experience (p < 0.01). Specifically, PW experience rated higher in autonomy supportive climate, autonomous motivation, perceived competence, and a greater emphasis on task approach goal orientation. Furthermore as a cohort, the students reported improvements in problem solving, collaboration and communication as a result of the PW experience. Finally, an exploratory hierarchical regression analysis revealed potential importance of perceived value, utilising meta-cognitive skills, and experiencing relatedness and autonomy in the prediction of skill development through PW experiences. The findings of this study present preliminary support the potential usefulness of outdoor and adventurous PW within a school context and provide implications for future research which are discussed further.