The cultural town of Cortona is packed with Renaissance architecture. Famous architects who have left their mark on this town include Francesco di Giorgio Martini and Giovanni Battista Infregliati (also called Cristofanello) and from the 15th century, Angelo and Francesco di Pietro and later Urbano da Cortona and Ciuccio di Nuccio as well as the architect Domenico Bernabei (also called Boccadoro).
Many would insist that it is impossible to find a large interesting town in Tuscany with rich medieval and Renaissance remains not overrun by tourists. But you can, and it is called Arezzo.
Montepulciano is about 60 km southeast of Siena. The town is built on the crest of a hill 605 metres above sea level. The town is Etruscan in origin, but became an independent province in the fourteenth century.
Sansepolcro nestles in the southeastern corner of Tuscany, just a few kilometers from Umbria and Marche. Although Sansepolcro is today an industrial town, the town centre is a great place to visit and abounds in rich medieval history.
At the top of a forest covered peak in Tuscany the monastery Monte Oliveto Maggiore stands in solitary majesty. You get here by driving up the winding country road before arriving at the impressive building complex. The monastery was built at the start of the 14th century when 3 Sienese noblemen and the holy Bernado Tolomei settled in this rugged place to pray and work.