A Study Tour is an opportunity for reflection in a new context. It emphasises experiential learning and offers both group and self-directed activities, enabling participants to explore new territories, cultures and people. It is a transformative reflectivce activity. This paper learns from the case study of a transformative experience for a group of Jamaican teachers and principals crossing the borders and engaging in a UK Study Tour. The evidence illuminates how teachers and principals might cross mental borders and widen their perspectives on the practice and leadership of education through experiential activities, and the ways teachers and principals can integrate new insights gained from crossing a border with existing knowledge from their side of their border. The main purpose of this qualitative reflective case study was to investigate the impact that Study Tours can have. The findings suggest that participants experienced remarkable personal and professional growth which are likely to result in significant changes to their practice and professional identity.