Many studies have recognized the political importance of Medici’s festivals during the age of the Grand Duchy. Starting from this assumption, this contribution intends to analyze certain 1589 wedding events from the perspective of Medici’s politics towards the Ottoman Empire and naval warfare against the Turkish corsairs. In particular, it focuses attention on the “Battle of Galleon,” which took place on April 25th, in Pisa along the Arno River, and the “Sea Battle” of May 11th, in Florence that was waged in the Palazzo Pitti’s Courtyard. From the comparison of official descriptions of these events with contemporary war chronicles, it is evident that scripts of both shows present a strict parallelism with real war practice. Besides, people who took part in them were effectively galley-slaves and seamen of Tuscan fleet. The similarity of these performances and their position in the Festival calendar (the first one right at the beginning, the second one at the ending) indicate an accurate strategy of communication from the organizers. They wanted to communicate an eminently political message, which was distinct from actions performed by Ferdinando I during his government: the increase of the fleet and the strengthening of the Santo Stefano Knights Rule, the improvement of Livorno’s seaport, and the intensification of the struggle against the Turkish corsairs at their strongholds.