Giovanni da Empoli's second voyage to Asia (1510–1514) was eventful and violent, characterised by the emergence of conflicting agendas among different groups of Portuguese. The Florentine merchant's long letter about the voyage is an extraordinary document, and provides insights in three important areas. First, it allows us to fill some of the gaps in the history of the early phases of Portuguese empire building, questioning the extent to which the Crown was pursuing a clear and coherent strategy that included the conquest of Malacca. Second, it problematises further our conception of “the Portuguese” by reporting episodes of Portuguese-on-Portuguese violence and opposing views on the objectives of Portuguese fleets in the Indian Ocean. Finally, Giovanni unequivocally expresses admiration for the international markets of Eastern city-ports and openly criticises the militarist attitude and lawless tactics of the Portuguese viceroy, Alfonso de Albuquerque, thereby inviting us to reconsider the chronology of a “cosmopolitan reaction” among Italian writers visiting South Asia.
