One of the most photogenic and interesting mediaeval parish churches in an area rich with romanesque parish churches is the Pieve (parish church) of San Polo in Rosso which dates back to the 12 C. The name of the church is mentioned in a donation of 1070 preserved at Badia di Coltibuono where it is referred to as Sancti Pauli Scito Russo

Montebenichi is located in the municipality of Bucine in the Province of Arezzo of Tuscany. The village is situated on a hilltop between the Chianti Aretino and the Chianti Senesi, dominating the Valdambra, right on the border with the municipalities of Gaiole in Chianti and Castelnuovo Berardenga. The views from the village are truly splendid, sweeping across the Crete Senesi to Monte Amiata in the south, Cortona in the east and Sienna and beyond in the west.

The Castle of Vicchiomaggio is in fact a splendid Renaissance villa incorporating the remains of a very early, probably Lombard, castle. It is also a producer of some of the best Chianti Classico wines – indeed, some of the best wines in Italy.

Badia a Coltibuono was founded in 1051 by monks of the Benedictine Vallombrosan Order who also began planting the first vineyards in the Upper Chianti area. In 1810, when Tuscany was under Napoleonic rule, the monks were forced to leave Coltibuono and the monastery was deconsecrated and, after passing through a number of hands, was bought by the Stucchi-Prinetti family.

Badia a Passignano. According to tradition, a monastery was founded at Passignano by Sichelmo in 890. An Abbey (Badia) was established 1049 as a consequence of the Vallombrosan monastic reforms, and took the form of a quadrangular fortified structure with corner towers.

Uzzano Castle is a fine Renaissance villa located on the outskirts of Greve in Chianti. Traces of the ancient castle may be discerned in the remains of a watch tower but the predominant form of the structure is now a large 17 C villa with an excellent italianate garden restored in the 18 C.

Villa Vignamaggio is located on the road to Lamole from Greve andPanzano. As it stands today, it is a splendid Renaissance villa rebuilt during the 15 C and the 16 C by the Gherardi family and showing a clear influence of the architecture of Brunelleschi.

Volpaia is a well-restored mediaeval village located in central Chianti. Part of the walls and two of the original six towers of Volpaia are preserved, the largest of the two housing the Castello di Volpaia wine shop and osteria. Volpaia was the hometown of a famous Florentine family of clock- and instrument-makers and is now an attractive tourist destination with three restaurants, a small grocery and some vacation rental apartments.

San Donato in Poggio is a mediaeval village of great charm located near the Via Cassia, the highway that runs along the western boundary of the Chianti Classico wine zone from Florence to Sienna. In modern times, the Via Cassia has been superceded by the Florence-Sienna motorway