Situated local knowledge and co-evolutionary processes overtake certitude and formal planning, challenging the way (cultural) heritage is produced in terms of both space and knowledge. This article contributes to the debate surrounding planning education and research by exploring the potential of inquiry-based learning (IBL) in spatial development and heritage conservation. The main argument is that the IBL format presented herein enables interaction and cooperation between various groups and their diverse sets of knowledge. To that end, the IBL approach was implemented both through project work and by creating a specific learning environment encompassing theory, exhibition, places, and people, and in which a research process was realised by students through iteration and reflection. The contribution systematises the results of a 2021 workshop held in Venice and Rome, including at the Corviale housing complex (Rome). In seeking to respond to the title-theme of the Venice Biennale, How will we live together?, initial evidence shows that educational activities stemming from clear research questions and “embedded” ways of inquiry-based learning present remarkable opportunities for participants to improve their ability to navigate into fragile and uncertain futures of the territory, engaging students in a wider process of knowledge-building.