The phenomenon of grey nomads travelling in rural and remote regions of Australia is on the increase, and as this cohort is an older age group, they are often travelling with chronic conditions, such as diabetes. Seven rural and remote diabetes educators were interviewed about their experiences of grey nomad travellers with diabetes, to whom they provided services. The findings revealed problems associated with grey nomads with diabetes, including maintenance of equipment, medications, self-management, glycaemic control and unpredictable events. The problems highlighted by the participants were exacerbated when travelling long distances for extended periods, often with changes to their usual regime of self-management. The isolation and remoteness of some areas was a factor for the travellers who were often not prepared and often turned to pharmacists for help. The participants were able to enhance the care and self-management of the travellers with diabetes and identified several pathways travellers may undertake if they needed services related to their diabetes. The diabetes educators’ capacity to provide services for travellers was stretched at times; however, this was viewed as positive in that it added diversity to their normal practice. Recommendations included a preparation checklist and information for travellers with diabetes and further education for pharmacists.