In 1488 the Emperor Maximilian had sent envoys to Spain to request Juana's hand in marriage for his son, Philip. However, it took until 1495 before an engagement was agreed. It then became a double 
engagement as Juana's brother, Juan, heir of Aragon and Castile, was betrothed to Philip's sister, Margaret. 
Juana's proxy wedding took place in Valladolid in early 1496. Dark-haired and quiet, Juana had been brought up in a devout manner and was two years younger than the 18-year-old Philip. Her ship landed 
in Arnemuiden in September 1496 but Philip was in Austria on behalf of his father. It took until the middle of October before they met. 
Juana immediately fell in love with Philip who was known as 'the Handsome'. Unable to wait, a dean was found to marry them quietly and that night the marriage was consummated. On 20 October 1496 they were again married with pomp and in public. Although their marriage was passionate, it also brought despair to the unstable Juana. 
On 16 November 1498 their first child was born, Eleanor, who would become Queen of Portugal and France. However, Philip started to lose interest in his devout, ever passionate but possessive wife and became promiscuous. Nevertheless, on 24 February 1500, their first son, the future Emperor Charles V, was born. 
However, much less fortunate was Juana's only brother, Juan, who, in 1496 had married Margaret of Austria, as he died only six months after their marriage. Juana's eldest sister Isabel, Queen of Portugal, 
was now heir of Castile and Aragon but died giving birth to a son, Miguel, but who lived for only two years, which made Juana heir of her. Juana and Philip were then pressured to come to Spain to take the Oath of the Cortes, obligatory to all heirs. In 1501, when another daughter was born to them, Juana became depressed, neurotic and highly hysterical. In November 1501 they went via France to Spain, leaving their children behind. While at Blois they met the French king with whom Philip went falconing and played tennis. 
By Easter 1502 they reached Madrid and soon Philip's men began to dislike the highly religious Spaniards. Also on their way to Toledo from Madrid, Philip contracted measles. While recovering at Olias, Juana's father arrived to an enthusiastic welcome from her. A week later they all went to Toledo to be joined by Juana's mother, the formidable Isabella. 
Soon they received the news that, first, Prince Arthur of England, husband of the youngest Spanish Infanta, had died; and second, the death of an uncle of King Ferdinand. The court went into mourning with vigour and, with Juana again pregnant, Philip was bored and so went hunting and playing chess with his father-in-law. 
Philip wanted to return to The Netherlands but it took until October before they were summoned to take the Oath. However, the Cortes would only accept Philip as Juana's consort, and then only during her lifetime. Philip then was left to preside over the Cortes who wanted to discuss war with Philip's friend, the King of France. By now Philip had had enough. He insisted on returning to The Netherlands, even if it meant leaving the heavily pregnant Juana behind. When told, Juana was hurt and lost control of herself. Nevertheless Philip still left and their son, Ferdinand, was born, 10 March 1503, at Alcala de Henares. 
Philip, realising that Juana could be manipulated by her parents, wrote asking her to come. On receiving this letter Juana went into ecstasy and, in the weeks that followed, the next stage of her madness 
appeared. When her mother suggested she stay in Spain, she went into violent rages and left on bad terms with her mother. 
When Juana arrived in Brussels she objected violently to Philip's new mistress and, in a fury, cut off the hair of the terrified girl. From now on Juana and Philip continually argued. At the end of 1504 the news arrived of the death of Juana's mother, which should make Juana Queen of Castile. However, as Philip wanted Castile for himself, Ferdinand, aware of Juana's instability, had the Cortes make himself regent.

Philip wrote first to Ferdinand, telling him to get out of Castile, and then to the Cortes advising them that Philip and Juana, the rightful queen, were on their way to Spain. Ferdinand then married again, hoping to father a son who would then be heir of Aragon, and so split Spain into two. After giving birth to another daughter, Juana was very ill. 
In January 1506 Juana and Philip set out by ship. Soon they were hit by a storm and forced to land in England. Henry VII welcomed them and invited them to Windsor where they stayed for over two months, during which Juana again became pregnant. 
Once arrived in Spain, Philip made himself popular and Ferdinand was forced to accept Philip and Juana as souvereigns of Castile, and, conceding that Juana was unable to rule, accepted Philip as actual 
ruler. Nevertheless, Philip was unable to convince the Cortes of Juana's madness. But then fate took a hand when, in September, there was a terrible heatwave. Philip had been playing his favourite game of 
"pelota" and, perspiring profusely, asked for cold water but began to feel unwell. The following day, although feverish, he still went hunting. After three days a chill set in. On the fourth day he was 
spitting blood, the six-months pregnant Juana spending most of her time with him. 

Philip was only twenty-eight when he died on 24 September 1506, which completely unhinged Juana. On 14 January 1507 she gave birth to their last daughter, Catharina. Juana had been told of a prince who had come to life after fourteen years in the grave, and so she watched over Philip's open coffin for fourteen years. As well, she would even travel around with the coffin, opening it at night.
 

Source: Leo van de Pas