Historical Centre Structure
Monte San Savino is encircled by a relatively well preserved scarp wall equipped with four doors. The main door, Porta Fiorentina, was designed by Vasari and built by Nanni di Baccio Bigio. A fresco depicting the Madonna delle Vertighe, San Savino and San Vitale can be seen on the lunette on the inside. Other doors are Porta Romana, Porta San Giovanni and Porticciolo Guglielmi.

The Cassero owes its present look (Sienese depressed arches and scarp walls) to the reconstruction carried out by the Sienese when they became lords of Monte San Savino in 1383.
Monte San Savino having fallen under the control of Florence in 1384, the lily of Florence was placed on the front of the fortress where it can still be seen.
As time went by, the fortress lost its purpose and housed a pawnbroker (end of sixteenth century) then a poor people’s home up to 1960. Entirely renovated in the seventies, the Cassero is now the City Museum, displaying ceramic vessels and various works of art, among which is a carved and painted Sienese wooden crucifix dating back to the fourteenth century. The premises are also used for temporary exhibitions and for public lectures.

Sainte Clare's Church
Saint Clare’s Church was built in 1652 adjoining the Cassero. It became private property in the eighteenth century and is now closed. Some works from Sant’Agata’s church (destroyed) and from the Society of Saint Anthony were transferred to Saint Clare’s at the end of the seventeenth century. Two side panels of a triptych by the Sienese master Matteo di Giovanni, depicting Saint Apollonia, Sigismondo, Rocco and Ansano; a valuable high relief by Sansovino glazed by Della Robbia showing the Virgin Mary with the holy Child and Saint Augustine, Romualdo, Lucia and Agata; an altar-piece by Sansovino showing Saint Lorenzo, Rocco and Sebastiano; a Christmas crib; a terracotta statue of Saint Anthony of the late Robbia school, are all kept in Saint Clare’s, along with a panting by S. Castellucci, The miracle of Saint Clare.

Di Monte Palace (Commune Palace)
The Di Monte Palace is built with ashlar-stone on the ground floor and follows the ionic order on the first, with windows having a triangular curved gable. The courtyard is encircled by an open gallery which has three arches on each side; two wells stand in the middle of the courtyard, by the shorter side of the arcade. A hanging garden, according to the wishes of Giovanni Maria di Monte (Antonio’s nephew) is to be found at the back of the building, the work of Giovanni di Baccio Bigio.
A precious sixteenth century door carved by Fra Giovanni da Verona can still be seen in the council chamber (the coats of arms of the most famous city families are painted on the walls of this chamber). The portraits of illustrious citizens of Monte San Savino and of former rulers of Tuscany (of which the most ancient nucleus dates back to the XVII century) adorn the corridors on the first floor.

The sinagogue is a very peculiar building. It has been restored various times and is located in a street now named after Salomon Fiorentino. It tells of the lasting influence of the Jewish community. The most ancient parts of the Synagogue date back to restorations carried out in 1729-32.