At the court of Urbino

In September 1504, having arrived in Urbino, Castiglione took up service at the court of Guidubaldo, where he was greeted by manifestations of great familiarity and friendship by the Duke, the Duchess Elisabetta Gonzaga and by their sister in law Emilia Pio. His duties were those of a cavalier and a diplomat; assigned the flattering and decorous title of “primario”, his was given command of a squadron of 150 soldiers, whom he leads in several missions.

Between November and December 1504 he went to Ferrara to visit the D’Este court; he discussed private business with Cardinal Ippolito d’Este, who held title over the fief from which the perpetual rights to Casatico, which benefited the Castiglione family.

During the first half of 1505 he lived in Rome, in the company of the Duke Guidubaldo, who together with Pope Giulio II was involved in political dealings and projects regarding the whole Italian situation. Here he was told about his first journey to England, as the representative of Guidubaldo during the official ceremony to nominate the Duke as one of the Knights of the Order of the Garter. Living in church buildings, he did not have a high opinion of the Rome of the prelates,frivolous and worldly, which he referred to a lot in his correspondence to his mother.

In April 1506 he was once again in Rome and, in view of his imminent trip to England, he received from Pope Giulio II his nomination to the Order of the Golden Spur, of which traces remain in the title Karus (or Charus) in his signature in this period.

Between 1505 and 1506, however, he receives the news of the premature death of his friend Domizio Falcone (fellow student during his stay in Milan), and then of his brother Gerolamo, both in the peak of their years. It was out of this double grief that his first great literary work was born: the Latin poem Alcon, one of the most acclaimed pieces of his Latin poems.