Once in the town, have a look at the buildings meant to protect the castle, such as the Tower and the Arch of Castruccio Castracani and the San Matteo Tower, built in the 1400s by the Florentine Republic and offering great views of the stunning surrounding countryside. On a particularly clear day even the sea is visible.
In the historic centre, a visit to the Palazzo Guicciardini Civic Museum is utterly unmissable. The archeological part of the Museum includes the Baldovinetti-Mainoni and Falchi collections, which boast Etruscan and Roman relics coming from all over Tuscany.
In piazza della Pieve is the Santi Giovanni Evangelista and Stefano Parish Church, an incredible gothic church which dates back to the beginning of the 14th century.
Other historic marvels include the San Sebastiano oratory, founded in the 16th century in the hope of saving the people from the plague, and the Church of Madonna del Soccorso, whose history is also closely linked to the same disease. Tradition dictates that a poor widower, whose wife died of the plague, heard the voice of the Virgin Mary here as she tried to console him; in her honour, he wanted to build a sanctuary. The Conservatory of Santa Maria is also lovely, home to impressive paintings.