Towards the end of the summer of 1220, Fernando requested and obtained permission to leave the Canons Regular of St. Augustine to embrace the Franciscan way of life. Although it is not certain whether he had personally met the first Franciscans to arrive in the Iberian Peninsula, he had certainly heard about them and found their way of life appealing.

At that time, the mortal remains of several Franciscans, who had been martyred for their faith in Morocco, had been placed in two silver chests and transported by Prince Pedro and his retinue to Ceuta. They were then transferred to Algeciras, then to Seville and finally to Coimbra, where they were laid to rest in the Augustinian Church of Santa Cruz.

The deeds of the martyrs were written down and miracles were spoken of, which increased devotion to Franciscanism among the local people. Fernando's request to join the followers of Francis of Assisi stemmed from a strong vocation to missionary life and, in particular, from his desire for martyrdom in imitation of these friars.

Anthony the missionary

In September 1220, Fernando removed the white tunic of the Augustinians and was invested in the coarse habit of the Friars Minor.

He abandoned his baptismal name for that of Anthony, the Egyptian hermit, after whom the Franciscan Hermitage of St. Anthony dos Olivais was named.
After a brief period of study of the Franciscan Rule, Anthony was sent to Morocco

The itinerary he followed is unknown. It is very likely that Anthony was accompanied by another friar, a standard Franciscan practice, however, this man too is unknown to us.

Having arrived in the territory of the Miramolino, in Marrakech, it is said that Anthony was welcomed as a guest into the home of a resident Christian family. To communicate with the Muslims, Anthony may have spoken Arabic, not so surprising as he had grown up in bilingual Lisbon, or he may have relied on the linguistic abilities of this companion.

However, because of an undetermined tropical illness, Anthony was unable to fulfil his mission preaching of the Gospel to the Muslims.

The illness was so severe that, while not giving up his aim of martyrdom, he was obliged to leave Morocco and to return home to Portugal.

But fate was again to play a part, when a storm and unfavourable winds carried the ship off course to Sicily. Tradition says that St. Anthony disembarked at Milazzo (Messina). As his talents were still unknown, his new community did not give Anthony any responsibilities. His Sicilian convalescence lasted for about two months.
Anthony then left Sicily for the Italian mainland to take part in the General Chapter being held in Assisi from May 30 - June 8, 1221. As a recent foreign recruit from Lisbon, Anthony was not known and probably spent the nine days of the assembly isolated and alone, immersed in observation and reflection.
When the General Chapter came to an end, none of the Ministers Provincial appeared interested in taking this undistinguished friar back with them to their jurisdictions. But Anthony was finally noticed by Friar Gratian, the Minister Provincial of Romagna. Having heard that the young man was a priest, Friar Gratian asked Anthony to come with him.

Hermit at Montepaolo

In the company of Gratian of Bagnacavallo and other friars from Romagna, Anthony arrived at Montepaolo in June 1221.

His days were spent in prayer, meditation and humble service to his brothers.

During this period, the future saint was able to mature his Franciscan vocation, renew his ascetic practices and purify himself in contemplation.

Most biographies state that Anthony remained at Montepaolo until Pentecost (May 22), or at the latest, until September of the same year.

Right from the start, given his obvious devotion, the brothers treated Anthony with reverence.

Having seen that one of his companions had transformed a grotto into a solitary cell, Anthony asked if he could use it.

Thus, every morning, after community prayers, Anthony hurried to his grotto (which is still carefully preserved today), to live alone with God in the discipline of penitence, intimate prayer, prolonged readings of the scriptures and contemplation.
For the canonical hours and for meals, Anthony joined his companions

But by his fervent penances he so exhausted his fragile health with fasts and vigils that, more than once, when the sound of the bell called him to community events, it is said that Anthony tottered in and would have collapsed had the other friars not held him up.

When Anthony asked how he could be of service to the community, the guardian of the friary assigned him to wash the crockery and sweep the floors.