Visual information has emerged as one of the main forces of the new age digital world and is even more critically influential in the touristic industry, wherein the perceptions and choices of tourists depend a lot on the appeal of the images. This study examines the role of mental images in shaping tourist preferences, focusing on the comparative analysis of two iconic destinations: Santorini the island of Greece and Sidi Bou Said the town in Tunisia. The two are very vivid in terms of culture and aesthetics despite the difference in context and tourism marketing. In this research, we adopted both quantitative and qualitative approaches to assess the effects of digital imagery on these travel destinations based on data retrieved from official sources and promotional materials; as well as questionnaires and interviews held among the tourists. The study reveals how potential tourist information processing is influenced and conditioned by the “mental images” constructed through and from digital media encompassing social nets, and virtual reality experiences. In both cases, these mental images—based on the imagery experienced online—are central for travel intention and planning. You will see how the contrasting promotional aesthetics—the sublime, exotic images of Santorini on the one hand, and the culturally saturate context of Sidi Bou Saïd on the other—help reveal how image makers employ different forms of visual appeal to create travel experiences that are most appealing to certain kinds of tourists. This paper is useful for tourism actors, as it enables the understanding of the role of consciously developed and implemented digital marketing communication, which increases the attractiveness of the destination and the emerging behavior of tourists. Finally, it identifies the summation that mental images with digital technology are important means of developing a competitive advantage in the tourism sector.