This paper explores the transitional experiences and challenges faced by girls from the Torres Strait Islands when they leave individual communities to attend boarding school in regional Queensland. The paper presents original ethnographic research using a narrative enquiry approach, capturing stories as narrated by a broad cohort of girls from within these communities, both past and present students. The stories relayed in this article are integral to assisting parents and extended family, staff and administrators to better manage the transition process from one community to another. Identifying the cultural, social and academic challenges associated with the transition process will enable those involved in student support both within the community and the school system to do so with an enhanced awareness so that the students involved may be helped to negotiate this experience more easily. This paper will also inform, although not directly engaging with the topic, the ongoing debate about the advantages and disadvantages of girls leaving their communities to attend boarding school. It will also add weight to the call to improve current strategies to assist with the transition process.