Travel and tourism is a booming sector of the 21st century world economy. Despite numerous positive trends, numerous critics deplore some developments in this industry. In an era of increasing leisure tourism or “part-time leisure tourism” tacked on to business trips, coming into contact with other cultures risks fading into the background. Therefore, the Travel Machine project of 2012 researched, analyzed, designed, and evaluated effective ways to foster a shift from leisure to cultural tourism by changing people’s travel behavior in the short- and in the long-term. The main objective is to persuade and motivate people, especially travelers aged up to 50 years, those from higher to average economic and educational demographics, to open themselves up more intensely towards the local population and culture of a destination, and to make out of their trip a deeper, personally enriching, and educational experience. For this objective, a well-designed mobile phone application prototype, the Travel Machine, was conceived by the author’s firm, combining information design/visualization and persuasion design. This chapter explains the development of the Travel Machine’s user interface, information design, information visualization, and persuasion design.