Urban resilience must consider the ability of cities to cope with the effects of climate change. Community awareness raising and sustainable urban drainage systems (SUDs) are often mentioned in the literature as effective adaptation actions while the success of these solutions is highly context-dependent and improved planning procedures are urgently needed. In this framework, the URCA! project represents a good practice aiming to strengthen the resilience of urban areas by promoting the implementation of SUDs in territorial planning. The main objective of the present research deals with the role of participation in promoting the use of SUDs and their uptake in town planning and land management involving local communities, students, experts, local authorities, and enterprises. To this end, the research adopts a participatory approach to SUDs urban planning for three case studies in Italy selected under the criterion of maximum variation (Brescia, Genoa, and Matera). For the three case studies, participatory approaches are at different stages of development thus requiring appropriate ways of interacting and resulting in different impacts on decisions. Preliminary results, drivers, and barriers in the application of the participatory approach are discussed and compared in order to bring innovation into planning practices, stimulating a revision of typical governance mechanisms.