Eleanore and Cosimo were married by proxy on 29 March 1539. No sooner was the agreement reached than the couple began to correspond. In May, Florencian agent Jacobo de' Medici was in Naples and informed the ducal secretary, Pierfrancesco Riccio, that "The Lady Duchess says she is happy and filled to the brim with satisfaction, and I want to assure of this." Riccio then added that when Eleanor received letters from her fiancé "she took pride in having understood them on her own, without anyone's help." She was quickly working on her reading knowledge of Italian, something she probably hadn't been interested in developing while living in a Spanish court. On 11 June, 17 years-old Eleanor set sail from Naples, accompanied by her brother Garcia with seven galleys following. They arrived at Livorno on the morning of June 22. That same morning, she left for Pisa and halfway through, met Cosimo. After a short stay in Pisa, the couple left for Florence, stopping for a few days at the Poggio a Caiano.