This paper shows the early results of a Participatory Action-Research (PAR) in which University, School, and Third Sector of the city of Palermo dialogue with each other to design new educational systems’ architectures. Within the theoretical framework provided by Universal Design for Learning, Outdoor Education and the Capability Approach, the chosen methodology is the informal conversation of the World Cafè. The working tables reflected on the implications of the intertwining among educational agencies, technological innovations, and territorial fabric. From these significant exchanges emerged perspectives of emancipation and co-construction of inclusive contexts for learning and social innovation