Developed within the framework of a multidisciplinary project, with active participation from the students of the Academy of Fine Arts of Reggio Calabria, “Pronti-Partenza-Vie!” is an innovative board game designed to turn the virtual exploration of a city's historic center—specifically, Reggio Calabria—into an educational experience for cultural and artistic purposes. The game employs a board with an urban map, cards, thumbtacks, and colored threads. Participants acquire knowledge of the toponymy of Reggio’s streets and the stories behind the figures and events that their names commemorate, through an engaging dynamic that combines specific quizzes, unexpected events, and wild cards. The ultimate objective is to create a work of art, consisting of a three-dimensional collage, rendered unique each time by the variable texture of the colored threads used to mark the players’ exploratory paths on the map. “Pronti-Partenza-Vie!” serves as a tool that stimulates cultural awareness and aims to promote interactive and engaging knowledge of a city’s core. It endeavors to incorporate each category of playful activity recognized in anthropological tradition: within a framework of healthy competition (agon), navigating elements of chance (alea), and virtually reconstructing the urban reality to which the game is directed through video support (mimicry). Participants learn, enrich their understanding, and engage with the excitement of discovery (ilinx). The educational significance of the game is acknowledged by modern pedagogy, emphasizing its role in the cognitive-social development of individuals. Likewise, Art History documents the use of playful activities to explore and disseminate aesthetic perspectives and artistic production across diverse civilizations. Thus, the proposed activity not only enhances knowledge of Reggio Calabria’s streets, but also effectively fosters and channels emotional connections with the city and its history.