This contribution seeks to present Gasparo Contarini’s diplomatic report (Relazione), made following three years in Venetian service in Spain between 1522–1525, to unfamiliar readers, as well as to elucidate its contents. It was a time when ground-breaking reports of the first global circumnavigation by Magellan/Elcano and conquests in the New World undertaken by Hernán Cortés were filtering back to the Spanish ruler, Charles V. Projects for the colonization of Brazil in neighbouring Portugal were afoot, as were attempts by other parties to reach the contested Spiceries by new routes. International juries were constituted to decide upon the division of the world’s spaces, culminating in the Treaty of Saragossa, and controversial maps were drawn up both to make sense of potentially new continents like the Americas, and to plead different cases at the upcoming tribunals. It is asked why such a polarized picture of successful Spanish and unsuccessful Portuguese imperial fortunes is provided by Contarini, at a time of great rivalry between Spain and Portugal, and it is suggested that Contarini – who did not personally travel to Portugal – may simply be following a rhetorical precedent fashioned by previous diplomats like Ca’Masser, Vincenzo Quirini and Pietro Pasqualigo. Historical, personal and documentary context (Contarini’s 400 dispacci, for example) is provided, and comparisons drawn to the letters and reports of other contemporary observers, like the Polish diplomat Jan Dantyszek at the Spanish court, as well as contemporary travellers and businessmen, like Jörg Pock in Lisbon.