The purpose of this research is to explore the complex and evolving orientations of cathedrals in the Iberian Peninsula and associated islands, examining the interplay between cultural, religious, political and architectural influences. Employing temporal and cultural analyses alongside remote sensing tools like Google Earth and HeyWhatsThat to gather archaeoastronomical data, over a hundred structures have been documented, revealing diverse orientation patterns across centuries. The earliest cathedrals aligned predominantly with equinoctial orientations in accordance with canonical prescriptions. However, deviations to the northeast appear from the 13th century onward, challenging conventional explanations and suggesting the need for a more in-depth analysis. Results suggest that cathedrals might be oriented according to ancient Roman city planimetries, to the perpendicular of the most employed qiblas during Muslim rule, and, naturally, to the ancient Christian prescriptions. In this context, the research sheds light on the potential influence of regional idiosyncrasies and pre-existing structures in shaping cathedral orientations, emphasizing the necessity of considering diverse cultural influences. Finally, a pivotal turning point around the last Council of Trent (1563) and the Gregorian reform of the calendar (1582) is identified, marking a relaxation in orientation prescriptions. Overall, this research contributes to a comprehensive understanding of the intricate history of temple orientations in the Iberian Peninsula within a broader cultural and historical context.