The Emperor set out from Valladolid on the 4th of November, 1556, at half-past three in the afternoon, after having dined in public, and forbidding absolutely that anyone besides his servants should take leave of him beyond the Puerta del Campo. In this second march he took an escort of cavalry and forty halberdiers. The first stop was at Medina del Campo, in the house of a celebrated money-lender named Rodrigo de Dueñas, who, like all those who unexpectedly become rich, was vain and ostentatious and wished to make a parade of his wealth, putting in the Emperor's room a brazier of massive gold, and instead of ordinary fuel fine cinnamon from Ceylon. This show, however, displeased the Emperor, and the smell of the cinnamon affected his throat, so he ordered the brazier to be taken away, and the money-lender to be paid for his hospitality, to humble his ostentatious, vulgar vanity. Another five marches brought them to Tornavacas on the 11th of November. Tornavacas is on the side of the range which bounds the Vera of Plasencia. From here it is only one march to Jarandilla, the next halt, but it was a very troublesome one, as a horrible defile, called the Black Pass, had to be traversed, which had no real road, only a track across torrents, by precipices, and through dark chestnut woods which covered the steep sides of the mountain.

The Emperor decided to follow this shorter but more difficult route, and left early on the 12th, preceded by many peasants with pikes and staves to make the way practicable. In front went the Emperor, sometimes in his litter, at others in his sedan-chair, or carried on men's shoulders, according to the state of the road. At his side walked Quijada, a pike in his hand, directing the march. Thus they went for three leagues.

The rest of the suite came behind without order and only careful not to leave their bones among the precipices. On arriving at the top of the Puerta the view of the beautiful Vera de Plasencia stretched before the gaze of the Emperor, and far away at the end of the valley on a little hillock, surrounded by orange and lemon trees, was the monastery of Yuste, which was to be his sepulchre. He looked on it for a time in silence, and then, turning round towards the Puerta, through which he had just come, said solemnly and sadly to Quijada, "I shall never go through another pass in my life except that of death."

The Emperor lodged in Jarandilla, in the castle of the Conde de Oropesa, D. Fernando Álvarez de Toledo, and stayed there three months, waiting until his rooms at Yuste were ready for him, and for money to pay the servants who had accompanied him so far, and who were not to follow him to the monastery. They amounted to about ninety, counting among them Italians, Burgundians, and Flemings. At last the Emperor definitely set out for Yuste, on the 3rd of February, 1557. At the door of his room he took leave of his servants, amid their tears, and with no little emotion on his part. After that everything was as silent and solemn as a funeral. Punctually at three o'clock he got into his litter, accompanied by the Conde de Oropesa riding on his right, Quijada on his left, and the Lord Chamberlain La Chaux behind.

The litter passed between two lines of halberdiers formed up at the gates of the castle, and no sooner had it passed than the guards threw down their halberds sorrowfully, as if they no longer wished to use these arms, after having done so in the service of so great an Emperor. The afternoon was rather foggy and the country dreary, and there was much that was impressive and funereal in the passing of this modest procession, which crossed the valley in silence and wound slowly up the hill on which the monastery stands. The litter stopped at the door of the church, among some orange trees, and the Emperor got out; they put him like a corpse into a chair and carried him up the steps of the High Altar. The Conde de Oropesa on his right, Luis Quijada on his left. The Prior, Fr. Martin de Angulo, then intoned the Te Deum. "The bells were overwhelmed and seemed to make more noise than usual," says the ingenuous account of the anonymous monk of Yuste.

The Emperor did not live at Yuste like a simple monk, as so many historians have averred. His household consisted of more than fifty persons, without counting the fifty-three friars who in various ways were connected with his service, and were selected with great care and sent to Yuste from the other convents of the Order. His house was large and comfortable, though not sumptuous, as can still be seen, for, thanks to its proprietors, the Marqueses de Mirabel, it remains intact. On one side it joined the church, the other three looked on the brothers' shady garden, which had been given up to the Emperor. The building consisted of eight big, square rooms, four on the ground-floor for summer, and four above for winter, which were those that the Emperor used. On each floor, from east to west, went galleries, the lower one running round both ends of the garden, the upper one leading to two large terraces, planted with flowers, oranges and lemons, and embellished with beautiful fountains, where, as in a stew-pond, were magnificent trout.

The rooms were hung with twenty-four pieces of Flemish tapestry, representing landscapes and scenes with animals. The study, or room, where the Emperor received was in the deepest mourning. At the time it was fitted up he was wearing mourning for his mother Queen Juana, so it was put up and so it still remains. It was hung with long black cloths and floating curtains and had a canopy and six big chairs of black velvet; twelve chairs of walnut and artistically worked leather, and six benches, which opened and shut, lined with black cloth. In the centre and almost under the canopy was a large table with a black velvet cover and an enormous arm-chair of a particular shape, with six very soft cushions and wheels to move it about, where the Emperor sat.

The bedroom had two beds, a big one and a little one, and a window in front which was also a door, and opened on to the same level as the High Altar of the church. Through it the Emperor heard mass from his bed when he did not get up, and through it the brothers came to give him the Pax and the Holy Communion when he received it, which he frequently did.

He had also brought some family portraits with him and some of his favourite painter Titian's wonderful pictures, rich jewels, and curious clocks by Giovanni Torriano, who was called Juanelo, and abundant plate for the use of his chapel, himself, and his table, little enough, however, for one who had exchanged the kingdom of two worlds for this corner.

The valets, barbers, cooks, bakers, and clock-makers, Juanelo and his assistant Valín, lived in a different part of the cloisters from that inhabited by the monks. The doctor Mathys, the apothecary Overstraeten, and the brewer Dugsen lodged in the hospice of the convent, while the secretary Martin Gastelu, the keeper of the wardrobe Morón, and Luis Quijada were boarded in the best houses of the village of Cuacos, whence they came each day to the monastery.