This study investigates the interaction effect between previous stopover visitation and assessment orientation on destination loyalty. Using a quasi-experiment, benefiting from a sample of 200 travelers with a self-reported stopover experience in Dubai, it is found that travelers high in assessment orientation are more loyal to the destination. The effect of previous visitation on destination loyalty is enhanced for high assessors. This research is the first to apply regulatory mode theory to the stopover destination context in the destination marketing literature. From a practical perspective, destination marketers should segment potential visitors using assessment orientation and target on high assessors who have previously visited the stopover destination.