In the UN Agenda 2030, tourism acquires a salient position as a critical sector, directly or indirectly influencing a number of Sustainable Development Goals (SDGs). The pursuit of Sustainable Tourism (ST) is founded on the respectful exploitation of the sector’s core ‘raw material’, i.e., the precious and vulnerable nexus of natural and cultural heritage, and a cooperative multi-actor endeavor of all those having a stake in this shared good. Strategic tourism policy decisions, formulated at the state level, frame actors’ actions, favoring a balance among economic, societal and environmental goals; and a transparent, concrete and supportive investment landscape, allowing the tourism sector to blossom. But how successful are these policy decisions in promoting a sustainable, resilient and durable tourism model by instigating the entrepreneurial community to invest in the vibrant culture–tourism complex? An effort to respond to this concern is made in this work, grounded in the ‘Culture–Tourism–Policy’ triptych and their interaction, the ‘policy cycle’ as a means of assessing policy performance towards establishing a sustainable/resilient ‘marriage’ of ‘Culture–Tourism’, and GIS-enabled spatial data management for an evidence-based assessment of policy outcomes. These three factors are closely intertwined in the assessment of strategic tourism policy decisions’ performance in a culturally vibrant and highly reputed destination, Greece.