This chapter examines how wine tourism strategies in Rioja and Mendoza are shaped through territorially specific development paths and why their resulting models resist direct transfer across regions. Drawing on comparative case evidence, the analysis shows that wine tourism is inseparable from the historical depth, environmental conditions, and institutional density that structure strategic choice in each territory. In Rioja, tourism evolves as an extension of consolidated production systems, where heritage, aging culture, and architectural continuity support strategies oriented toward symbolic depth, reputation management, and controlled experiential renewal. In Mendoza, wine tourism follows a more outward-facing logic grounded in altitude, aridity, and irrigation-based agriculture, where landscape exposure, environmental contrast, and scientific narratives become central resources for international positioning and differentiation. The chapter further demonstrates that organizational design, production–tourism relations, and risk management reflect these territorial logics, producing distinct meanings of success that cannot be reduced to generic performance indicators. Success in Rioja is associated with continuity, prestige control, and cultural legitimacy, whereas in Mendoza it is linked to visibility, experiential intensity, and the translation of environmental extremity into market value. The findings confirm that wine tourism strategies emerge from long-term spatial, institutional, and cultural alignment rather than from transferable best practices, reinforcing the importance of territorial specificity for understanding strategic outcomes in wine regions.