Cultural Landscapes, resulting from a long history of interaction between people and nature, are a well-recognized resource for improving the quality of life and promoting sustainable economic chains. However, the current Climate Change process, putting the fragile equilibrium between the natural and human environment at risk, represents one of the most significant threats to their conservation. In particular, due to their dependence on specific combinations of cultural and environmental factors, the Wine Cultural Landscapes requires effective strategies to safeguard their tangible and intangible components. In this context, the research aims to provide decision-makers with a methodological framework for exploiting the potential of geospatial data in evaluating the adaptability of Wine Cultural Landscapes to the environmental transformation produced by Climate Change. Moving from the existing policies and the most common indicators for landscape assessment in the European framework, the research proposes a data-driven workflow to evaluate the transformation of Wine Cultural Landscapes to support the activation of dynamic conservation strategies (ICOMOS, ICOMOS-IFLA principles concerning rural landscapes as heritage, 2017). The paper considers, as applicative case studies, two European Wine Cultural Landscapes through a comparative approach: the Rioja (Spain), included in the UNESCO candidate list, and the Colli Tortonesi (Italy), an Italian Protected Origin Denomination wine production area.