Knowing and orienting oneself on a reference territory is a challenge that crosses different perspectives and ways of interpreting times and living spaces. For this reason, an intercultural pedagogist and an art historian, expert in iconology and cultural heritage, decided to work on the exploration of the city of Macerata, through the development of the Urban Ticass and Urban Ticass 2.0 projects. These activities have promoted the cooperation of the university and schools, looking for details and significant contexts within the city walls, as well as in meaningful places for those involved. The initiatives carried out have verified the centrality of the notion of detail and context in the cultural heritage sector, fuelling reflection also in a pedagogical perspective. Starting from the meanings emerged, historical reconstructions in an educational key have been developed, relying on laboratory and experiential teaching. At the end of both projects, the students involved the territory through playful and educational urban explorations open to citizenship as a widespread and contextualized learning model.