Abstract In 1593 Francesco Maria II della Rovere, Duke of Urbino, sent a number of diplomatic gifts to Philip II of Spain, intended for the crown prince, the future Philip III. The gifts included a silver model of a citadel accompanied by a set of compasses, the whereabouts of which are currently unknown; a small gilt-bronze sculptural group which has been identified with Giovanni Bandini’s The Hunt, today in the Prado Museum; and an illuminated manuscript recounting glorious episodes from the reign of the Emperor Charles V, Philip III’s grandfather, identified with British Library, Add. ms 33733, which contains miniatures possibly by Simonzio Lupi. A study of some of the inventories made in Madrid at the beginning of the seventeenth century has revealed that The Hunt and the illuminated manuscript might subsequently have belonged to persons close to the Duke of Lerma, Philip III’s prime minister – namely, Juan de Borja, the duke’s uncle, and Jerónimo Funes, the son-in-law of the secretary of state, Count of Villalonga, respectively.