The continuous transformations that characterise cities have placed at the centre of the political debate the theme of urban regeneration, as urban, environmental, and social rehabilitation, especially about degraded urban areas that become fertile ground for new urban functions. Considering degraded areas as the result of economic, social, physical, and environmental transition processes, their regeneration must consider an inclusive and multi-actor process involving different stakeholders and users. Such an understanding examines multiple cultural and design approaches to urban regeneration and geographical transformation. This paper implements the Geodesign approach to investigate and develop a Collaborative Decision Support System oriented to the planning and assessing wasted roadscapes regeneration. The wasted roadscapes are conceived as degraded areas located close to roads, which need sustainable strategies with particular attention to local problems related to accessibility and the inclusion of degraded areas in the planning process. Bacoli’s city (South of Italy), has been selected as a best-fit case study for testing the decision-making process elaborated, involving a working group of professors, researchers, PhD candidates, students, local authorities, and citizens. The Geodesign approach facilitated the definition of sustainable planning strategies among people with diverse backgrounds and interests, aiming at recovering degraded landscapes and connecting them to urban accessibility strategies, facing conflicts and supporting the elaboration of a shared vision.