This theoretical study aims to provide a learning model for adventure tour guides to become effective learning facilitators for adventure tourists, who have increasingly sought self-transformation through soft-adventure activities. This objective is drowned by the increasing interest in learning from different cultures among adventure tourists and also the attention to self-transformation through pedagogy, adventure tourism, outdoor adventure education (OAE), and pedagogy are becoming increasingly capable of sharing their theories under the concept of cross-boundary learning. This paper therefore organizes this sharing by considering the applicability of OAE theories to soft adventure tourist based on literature review. It then centers on the community of practice created from interaction between guides and tourists and between tourists as a way of learning, which can lead adventure tourists towards self-transformation, and discusses how guides can create opportunities for such cooperative learning community during their service. As a result, taking a cue from the SECI model, which underlies cross-boundary learning, a conceptual model was presented to implement the facilitator role of the guide in cross-boundary learning effectively. In this conceptual model, the guide’s role extends beyond knowledge transfer. Rather, the results of the study imply that guides are required to be co-creators of knowledge to accompany adventure tourists in their cross-boundary learning. The findings also suggest that guides need to become cross-boundary learners who may also learn from their customers.