The concept of transformative resilience emerges from complex recent literature and represents a way to interpret the potential opportunities to change in vulnerable territories, where a socio-economic change is required. This article extends the perspective of transformative resilience to assessing of the landscape multi-functionality of inland areas, exploring the potentials to identify a network of synergies among the different municipalities able to trigger a process of territorial resilience. A Spatial Decision Support System (SDSS) for multi-functionality landscape assessment aims to support the local actors to understand local resources and multi-functional values of the Partenio Regional Park (PRP) and surrounding municipalities, in the South of Italy, stimulating their cooperation to the management of environmental and cultural sites and the co-design of new strategies of enhancement.