This paper offers an in-depth account of how sustainable initiatives are assembled and function in practice, using the city of Cesena in Northern Italy as a case study. Located along the Savio River, Cesena’s cultural identity and urban development have long been shaped by its close relationship with the river and its surrounding biodiversity. This connection, however, has been increasingly tested by environmental crises, most notably the devastating flood that severely impacted the region in 2023. In response, the project aims to establish a collaborative public–private governance scheme that fosters closer cooperation between local residents, municipal authorities, and key stakeholders. Special attention is given to engaging the community in shaping the district’s sustainable future, with an emphasis on resilience, inclusivity, and environmental awareness. The paper also investigates the often-overlooked dimensions of local sustainability efforts and evaluates their broader societal impact using the New European Bauhaus (NEB) Impact Model as a framework for assessment and reflection.