This chapter examines the territorial conditions that shape wine tourism strategies in Rioja and Mendoza, arguing that producer choices can only be understood in relation to the historical, environmental, and institutional contexts in which they are embedded. In particular, it reconstructs the long-term evolution of Rioja as a wine region marked by deep historical sedimentation, regulatory consolidation, and climatic moderation, where viticulture, aging culture, and export orientation have generated a dense symbolic economy. Within this setting, wine tourism develops as an extension of established production systems and tends to emphasize heritage interpretation, cellar time, and reputation management. The chapter then analyzes Mendoza as a contrasting territorial model structured around aridity, altitude, and irrigation governance. Here, viticulture depends on technological control of water and environmental adaptation, and the region’s development follows more discontinuous trajectories shaped by immigration, agro-industrial expansion, and export-led repositioning. Wine tourism in Mendoza is closely linked to landscape visibility, technical mastery, and the communication of environmental distinctiveness in global markets. The comparative discussion brings these contexts into dialogue to show how climatic regularity or extremity, institutional thickness or flexibility, and continuity or transformation shape the strategic vocabulary available to wineries. The chapter demonstrates that wine tourism strategies emerge from long-term territorial alignments rather than isolated managerial decisions, defining both the limits and the possibilities of experience design, credibility, and strategic differentiation in each region.