Tourism pressure emerges as a significant issue in mainstream tourist destinations. On one hand, the increasing tourist presence offers an opportunity for the development of the local economy driven by external agents; on the other hand, excessive sectoral specialization leads to challenges related to the sustainability of places. This paper presents a case study applying the STESY model to Dubrovnik, Croatia, a globally recognized cultural destination facing critical challenges related to overtourism, spatial imbalance, and seasonal pressure. The research focuses on identifying and rebalancing tourism aiming to reveal latent opportunities for sustainable and inclusive development. Particular attention is given to the Canal d’Ombla area, proposed as a strategic Destination area within the broader tourism ecosystem of Dubrovnik. The strategic framework was developed through a collaborative design studio with architecture students from the University of Basilicata, integrating interpretative approaches with data-driven territorial analysis. Framing tourism as a key component of spatial planning, the study advocates for a context-based decision support system aligned with the principles of the New Urban Agenda. The paper details the methodological process, the spatial taxonomy of DAj, and a development proposal titled “DUBROVNIK and the cities of CANAL D’OMBLA”. The discussion outlines key findings, methodological limitations, and future directions for sustainable tourism governance in fragile cultural landscapes.