Internationally, the population is ageing and people are living well, longer. In Australia, extended travelling has gained popularity among older Grey Nomads due to time and opportunity post retirement. However, there is limited research available focusing on older Australians’ health while travelling. This paper reports the qualitative phase of a larger mixed-method project that explores the experience of Australian Grey Nomads travelling with chronic conditions. Eight Grey Nomads participated in telephone interviews. Data were analysed using inductive thematic analysis. Two themes emerged, namely: continuity of care while travelling and experts on the road. Participants described encountering a fragmented health system, with challenges regarding finding health services; a lack of shared medical records; and difficulties accessing regular medications. Despite these challenges, participants demonstrated health preparedness, an ability to accommodate health on the road, and were all travelling for their health. This study highlights key systems issues that challenge health care while travelling, and identifies opportunities for both usual practices and rural health services to enhance the care provided to this group.