This paper reflects on ways of updating tools for engagement and enhancing citizens’ participation in local urban planning, and aims to reshape them according to theories that have emerged in recent decades on the conceptualization of such participation and on interdisciplinary methodologies. It does so in the context of a project investigating how local institutions try to produce new forms of engagement. The project was carried out in the Municipality of Peccioli, an ancient medieval village in Tuscany, Italy. We have revisited and combined some classical tools, such as documentary investigation, participant observation, focus groups and interviews, and proposed changes for capturing unexplored features, dimensions, and living experiences in the social body. The updating of classical methods aims to overcome existing power structures and to reshape the relationship between citizens and their local institutions, generating a more inclusive decision-making process.