[4] In 1494, at the age of sixteen, Castiglione was sent to Milan, then under the rule of Duke Ludovico Sforza, to begin his humanistic studies at the school of the renowned teacher of Greek and editor of Homer Demetrios Chalkokondyles (Latinized as Demetrius Calcondila), and Georgius Merula.

The hosts and guests organized intellectual contests, pageants, dances, concerts, recitations, plays, and other cultural activities, producing brilliant literary works.

Castiglione wrote about his works and of those of other guests in letters to other princes, maintaining an activity very near to diplomacy, though in a literary form, as in his correspondence with his friend and kinsman, Ludovico da Canossa (later Bishop of Bayeux).

He and the new Duke, who had been appointed capitano generale (commander-in-chief) of the Papal States, took part in Pope Julius II's expedition against Venice, an episode in the Italian Wars.

That Castiglione's love for Ippolita was of a very different nature from his former platonic attachment to Elisabetta Gonzaga is evidenced by the two deeply passionate letters he wrote to her that have survived.

In 1524 Pope Clement VII sent Castiglione to Spain as Apostolic nuncio (ambassador of the Holy See) in Madrid, and in this role he followed court of Emperor Charles V to Toledo, Seville and Granada.

While in his letter to the pope (dated 10 December 1527), he had the audacity to criticize Vatican policies, asserting that its own inconsistencies and vacillations had undermined its stated aim of pursuing a fair agreement with the emperor and had provoked Charles V to attack.

It was designed by the mannerist painter and architect Giulio Romano, a pupil of Raphael, and inscribed with the following words:Baldassare Castiglione of Mantua, endowed by nature with every gift and the knowledge of many disciplines, learned in Greek and Latin literature, and a poet in the Italian (Tuscan) language, was given a castle in Pesaro on account of his military prowess, after he had conducted embassies to both great Britain and Rome.

While he was working at the Spanish court on behalf of Clement VII, he drew up the Book of the Courtier for the education of the nobility; and in short, after Emperor Charles V had elected him Bishop of Avila, he died at Toledo, much honored by all the people.

[9]The Humanist spirit, with its longing to embrace and fuse the variety and confusion of life, fills that Renaissance conversation – at once so formal and so free, so schooled and spontaneous, so disciplined in design and convivial in movement – with an ardent vision of the one virtue of which human nature is normally capable: that of moral urbanity.

The book, in dialog form, is an elegiac portrait of the exemplary court of Guidobaldo da Montefeltro of Urbino during Castiglione's youthful stay there at the beginning of the sixteenth century.

It depicts an elegant philosophical conversation, presided over by Elisabetta Gonzaga, (whose husband, Guidobaldo, an invalid, was confined to bed) and her sister-in-law Emilia Pia.

The genre is also the same in The Courtier and De Oratore: a comfortable, informal, open-ended discussion, in Ciceronian rhetoric called sermo (conversation),[16] in which the speakers set out the various sides of an argument in a friendly (rather than adversarial) way, inviting readers, as silent participators, to decide the truth for themselves.

"[19] The aim of Castiglione's ideal Renaissance gentleman was not self-cultivation for its own sake but in order to participate in an active life of public service, as recommended by Cicero.

To do this he had to win the respect and friendship of his peers and most importantly of a ruler, or prince, i.e., he had to be a courtier, so as to be able to offer valuable assistance and disinterested advice on how to rule the city.

At the outset of the discussion Canossa also insists that the art of being a perfect courtier is something that cannot be taught (that is, broken down to a set of rules or precepts), and therefore, he declares (rhetorically – and with sprezzatura) that he will refuse to teach it.

The other participants eventually agree that even someone who is lowly born can be a perfect courtier, since nobility can be learned through imitation of the best models from life and history until it becomes ingrained and natural.

The participants also deplore what they consider the rude and uncultivated manners of the French, who they say look down with disdain on what they call a "clerk" (or someone who can read and write), though hope is expressed for Francis of Valois, the future king of France.

There is a long discussion, too, about what are appropriate topics for joking (pleasantries), an essential component of pleasing conversation: one should not mock people's physical attributes, for example.

For when all is said and done, the very fabric of the universe, which we can contemplate in the vast spaces of heaven, so resplendent with their shooting stars, with the earth at its center, girdled by the seas, varied with mountains, rivers and valleys, and adorned with so many different varieties of trees, lovely flowers and grasses, can be said to be a great and noble painting, composed by Nature and the hand of God.

[25] The following evening Giuliano di Lorenzo de' Medici, who at age 28 is a bit more mature than Gaspare Pallavicino, is chosen to defend women.

He rises to the occasion, affirming their equality to the male sex in every respect, and he points out how throughout history some women have excelled in philosophy and others have waged war and governed cities, listing the heroines of classical times by name.

[29] He talks about the divine nature and origin of love, the "father of true pleasures, of all blessings, of peace, of gentleness, and of good will: the enemy of rough savagery and vileness", which ultimately lifts the lover to the contemplation of the spiritual realm, leading to God.

[30] When Bembo has finished, the others notice that they have all become so enraptured by his speech that they have lost track of the time, and they rise to their feet, astonished to discover that day is already dawning:So when the windows on the side of the palace that faces the lofty peak of Mount Catria had been opened, they saw that the dawn had already come to the east, with the beauty and color of a rose, and all the stars had been scattered, save only the lovely mistress of heaven, Venus, who guards the confines of night and day.

From there, there seemed to come a delicate breeze, filling the air with biting cold, and among the murmuring woods on neighboring hills wakening the birds into joyous song.

It was one of many Italian dialogues and treatises written during the Renaissance that explored the ideal gentleman, including Stefano Guazzo's Civil Conversation (1581) and the Galateo (1558) by Giovanni Della Casa, the sourcebook for later etiquette guides.

Queen Elizabeth's tutor and later secretary, Roger Ascham, wrote that a young man who carefully studied The Book of The Courtier would benefit from it more than from three years travel in Italy.

[33] Later commentators have not infrequently accused it of advocating superficiality (with "slight justice" according to June Osborne), yet it has also been called, “The most important single contribution to a diffusion of Italian values” throughout Europe.

Castiglione's letters not only reveal the man and his personality but also delineate those of famous people he had met and his diplomatic activities: they constitute a valuable resource for political, literary, and historical studies.

[35] Painting possesses a truly divine power in that not only does it make the absent present (as they say of friendship), but it also represents the dead to the living many centuries later, so that they are recognized by spectators with pleasure and deep admiration for the artist.