This paper addresses the dearth of research into the roles high school teachers play in organising and leading international study tours offered by high schools in New Zealand (prior to the COVID-19 pandemic). The aim of this paper is to provide insights into the motivations and experiences of teachers involved in these tours. A grounded theory approach was used, and qualitative data were collected via face-to-face interviews with eight teachers forming the basis of the development of a theory which proposes that both navigating and negotiating learning experiences are key aspects of the teacher’s role. Data revealed that the expectations and challenges placed upon the teachers had implications for their personal and professional lives. The tension between teachers’ perceived obligations for the safety of the students and the adolescent’s desire for freedom to explore whilst travelling proved difficult to resolve and teachers questioned the sacrifices they personally needed to make.