The Basilica of Santa Margherita is dedicated to the patron Saint of Cortona “Santa Margherita” and it is located on the top of the hill. Margherita had a peculiar story. At the age of 17 she felt in love with a young man, called Arsenio. From this union a baby was born, but outside of marriage. This was a strange and awful situation in the Middle Age. In 1273, during a hunting trip, Arsenio was killed, and she was repudiated by his family. So, she was all alone with a baby, and the best solution is to retire to a convent. She came to Cortona, and entered in the city through Porta Berarda, a door that is still visible nowadays. She was hosted by the Franciscan friars of the monastery of San Francesco. On that place she also founded the hospital (that had been working until about 30 years ago). When the Saint dead, the 22nd of February 1297, the people who lived in Cortona decided to build a church dedicated to her, next to the ancient little church of San Basilio, that Margherita restored after choosing it as place of penance and prayer. She loved this isolated place, near Cortona, where it is possible to see all the Valdichiana. The works for the construction of the church began in 1297, but they finished in 1304. The church has undergone many changes during the ages. The present building is the result of the nineteenth century reconstruction. From the original medieval church remained only the rose window in the façade, the bell tower and the external wall of the choir. People of Cortona and of Val di Chiana celebrate Santa Margherita on the 22nd of February of each year. From the church of Santa Margherita, you can admire all the landscape with a 360°degree view on the beautiful Val di Chiana.

The church of Santa Maria delle Grazie al Calcinaio is a stunning church located in the lower part of the hill of Cortona, outside the city, in a place named Calcinaio. On this location during the Good Friday in 1484, a picture of the Virgin Mary with the Baby, painted on a wall of a tub used for the dressing of leather (called by people of this area “calcinaio” because of the quicklime used for this purpose), started to make miracles and healings. You could also see nowadays this picture on the main altar of the church. After the people devotions to this image, and after the offers in honour of the Virgin Mary, the Corporation of Shoemakers, who have on that place their lime thanks, decided to build a church dedicated to the Virgin Mary. The project was given to many architects, but they all rejected to build it for the steep terrain and the flow of water. Then the architect Francesco di Giorgio accept to build the church. It also seems that the famous Leonardo da Vinci took part in the design. The works started in 1485, and in the first quarter of 1500, the church reached its final version, at least in the exterior part. The last works continued slowly; in fact, the main portal was finished in 1543. When you enter inside the church, what affects you the most will be the light, that rains from the top, spreads on all the extension of the church. This is the reason why the visit is suggested especially in the morning and during the sunny day. The structure of the church has got a unique aisle flanked by two side chapel with a transept and a dome from the intersection of the presbytery equal beams.
The church is essential in its construction and what makes it so beautiful is its simplicity. Its architecture has got white and grey lines and arches that cross over each other.
Inside and outside the church there are references to Brunelleschi, one of the most famous architects in Italy during the Renaissance period.