This paper aims to assess the territorial resilience of a socio-ecological system through an innovative integrated evaluation framework to aid the decision-making process in the planning of transformation scenarios. This framework employs a set of resilience indicators through a Multicriteria Decision Analysis (MCDA) coupled with a Lotka-Volterra mathematical model of cooperative type. The set of indicators aims to calculate a composite index of Territorial Resilience (TRI), whereas the mathematical model is an extension of an existing model, aimed to predict possible long-time scenarios. The proposed operational framework for rural and vineyard landscapes aims to bridge the existing gap between territorial resilience theory and practice, with an innovative Decision Support System able to assist Decision Makers and territory planners in the planning and management of resilient territorial systems. This integrated evaluation framework is applied to a famous wine region in Portugal, the Douro Valley, where Port-wine grows. Such framework, especially in a context of adaptive governance, proves to be a suitable support in the field of landscape and urban planning to evaluate the dynamics of socio-ecological systems and to envision long-term policies and actions.