Sustainable development strategies at urban and regional levels encompass a multidisciplinary discourse integrating global perspectives with practical insights into sustainable urban planning, land use, transportation, and ecological design. Addressing the tensions between economic growth, social equity, and environmental preservation, current trends in policy recommendations draw from international institutions and academic research. Tourism emerges as a pivotal sector in urban sustainability discourse, shaping policy and design across multiple scales and stakeholders. This paper presents a case study applying the STESY model to in Andalusia (Spain) a region witnessing substantial growth in its tourism industry. With eno-gastronomic and cultural tourism as its focus, the study employs open data and cluster analysis to identify local tourism Destination Areas, guided by a strategic framework developed through collaborative efforts with architectural students from the University of Basilicata. Focusing on tourism as a critical component of territorial planning, the paper advocates for a decision support system aligned with the New Urban Agenda, emphasizing context-based design and sustainable development principles. The methodology outlines the STESY model application, culminating in a proposed development strategy titled “Sherry Triangle” aimed at enhancing Andalusia’s tourism ecosystem while preserving its local identity and sustainability. Discussions and conclusions highlight research insights, limitations, and future directions for sustainable tourism development.