The Basilica of St Bernardino all'Osservanza

Bernardino at the Capriola

Bernardino’s long stay at the Capriola, the hill where the Basilica dell’Osservanza stands, was intermittent and can be divided into two periods: the first was between 1405 and 1415, the second went from the spring of 1425 to that of 1444.
We know very little of the first period. It was characterized by a strictly ascetic life of prayer, penance and care of his brothers, for whom he humbly begged. This is where Bernardino studied and practiced preaching.
On May 1st 1404 he held his first public sermon in Siena, in the small Franciscan church in Alberino, and on June 11th he preached at the hospital chapel of Sant’Onufrio, in what today is known as the Via del Sasso di Saint Bernardino, in reference to the fact that he used to address his followers while standing on a stone. In memory of this sermon, a polychrome terracotta bust of the saint - now in the Oratorio di Sant’Anna in Sant’Onofrio -  was placed outside the building. 
After a deanery in Tuscany, in 1417 divine inspiration urged him to dedicate his life to preaching and he set off to northern Italy. His departure to Genoa commenced the golden age of his evangelism and the dissemination of the Observance in northern Italy.
During Bernardino’s second stay at the Capriola (1425-1444) the hermitage was definitely transformed into a friary, even on account of the massive amount of conversions that followed the saint’s vigorous evangelism.