The article examines the first circumnavigation of the globe (1519-1522) in light of the recent quincentenary celebrations, focusing on changes in its historiographical interpretation and cultural memory. Drawing on the author’s editorial work on Antonio Pigafetta’s Relazione, the study reflects on the evolution of research tools and on new political and cultural sensibilities surrounding the very notion of “discovery.” The Magellan–Elcano expedition is reassessed as both an extraordinary navigational achievement and a political and commercial failure, highlighting its crucial role in revealing the true dimensions of the globe and in triggering early processes of globalization. Particular attention is devoted to the Philippine context, the death of Magellan, and the divergent memories that emerged from it, embodied in the figures of Lapulapu and Enrique of Malacca. The article concludes by exploring contemporary artistic and symbolic reinterpretations of these events, showing how the past remains a contested field between historiography, postcolonial identities, and practices of memory.