© 2020, © 2020 Informa UK Limited, trading as Taylor & Francis Group. Despite stopovers being a part of long-haul air travel since commercial flights commenced over 80 years ago, the first published research on the phenomenon did not appear until 2016. Also, even though destination image has been the most researched construct in the destination marketing literature, no studies had measured perceptions of a destination in the context of a stopover until 2018. This study makes a contribution to this emerging research field by reporting how a quasi-experimental design found previous visitation enhances destination image and destination loyalty in the context of a stopover during long haul international air travel. However, this effect was weakened for individuals high in prevention focus. Conceptually, the research design is underpinned by Regulatory Focus Theory, which has rarely been reported in the destination marketing literature. The results have practical implications, for Dubai as a stopover destination, and for other destination marketing organizations responsible for emerging destinations or destinations in regions that have experienced negative publicity.