The construction of the Loggiato, in the background of the Piazza del Municipio, dates back to 1513 when the representatives of the Castiglion community appointed the master masons, Bernardo del Ghirba and Fillipo Bellinzona, to build a loggiato with stone mouldings and arches.
The traditional attributions to Vasari are justified by the restoration that was done between 1560 and 1570, the period in which the Medici coat of arms was placed and also during which the typical architectural characteristics were white plaster with stone mouldings. In 1733, for static reasons, the arches looking onto the Val di Chio were walled and they were only reopened in 1922. On the closed sides of the loggia, the coat of arms of the Commissary and the Florentine Mayor can be seen in Della Robbia terracotta or in sandstone. On the left a damaged fresco of the Annunciazione can be found, a copy of the one in the SS. Annunziata in Florence.