The ‘Southern Milan exploratory tour from the southern Electrical Substation to Fondazione Prada’ and the ‘Exploratory tour of the Chiesa Rossa, Stadera and Morivione neighbourhoods’ are free tour guides for mobile devices created by students in the school-work programme at the Istituto C. Varalli and in mixed groups of the Istituto Tecnico per il Turismo and the Liceo Linguistico. Discovery and exploration of the territory along the itineraries was followed by documentation of the cultural heritage and development of communication designed for a wide audience of young people and adults, including fellow students, parents, citizens, and tourists, including foreigners. The result was two itineraries whose stages consist of elements in the cultural landscape, which were explored, mapped, studied, and communicated by the students in two languages. The tours were built using the Izi.TRAVEL platform, a professional, open-access CMS (content management system) for tour operators. The tool allows tourists to immerse themselves in exploring the landscape along the route, identifying points of interest using a GPS positioning system and audio guide. Once the students had been trained, the intuitive back end allowed them to work independently and apply what they had learned in different contexts, such as planning educational trips.