Volpaia was recorded for the first time in 1772 in a document from the Abbey of San Lorenzo a Coltibuono as the "Curte et Castello di Vulpaia". The original defense walls, laid with great precision out of local pietra arenaria (sandstone), date back to the end ofthe XII and beginning of the XIII centuries. It was not until the first half of the XIV century however, when the castle became one of the main centers of the Lega del Chianti, the Chianti League, in the Radda area, that it assumed a role of any real importance. Because of its favourable and dominative position it was soon equipped with a true surrounding wall in the form of a rough ellipse with the defense towers rising up in a quadrangular arrangement. Today only a part of this wall and a small later-dated tower to the north are still visible. There is no trace of the gate which probably corresponded in the
defense wall with the street dividing the area into two parts. Only gradually-especially around 1500 to 1600 - did the castle lose its purely defensive function, new gates then being constructed. The parish church, dedicated to San Lorenzo since the XIV century, has a sextangular arch. At the summons of the castle lord the Commenda di San Eufrosino was established in 1443 outside the gare of the ancient castle, in order to shelter and provide care for pilgrims and wayfarers. The site of the hospital is indicated by a Maltese cross carved under an architrave. The edifice shows characteristics of the early FIorentine Renaissance such as the simple rectangular structure and the contrast between the grey of the pietra serena (local grey sandstone) used for the omamental elements and the white of the walls. There Were very few buildings outside the surrounding wall and those few were all only mentioned for the first rime at the end of the XVI century.

The surroundings of Radda in Chianti have several interesting place to visit: an half day tour can be dovoted to visit the Castello di Monterinaldi, Castello di Volpaia, Castello d'Albola and Santa Maria Novella and Montevertine