The little town with Etruscan origins is situated on the Chiantigiana road, the SS 222 between Castellina and Greve. 
During the second half of the 10th century, members of Chianti`s landed aristocracy began building castles, or fortifications, from which to defend their properties. The years between the middle of the 11th century and the early decades of the 12th century saw the highest rate of construction of such fortifications, one of which was the Castle of Panzano.
The seigniors, who chose the site for construction of the castle, were most probably members of the Firidolfi family.
Within a brief period of time, the castle became the focal point for population growth in the area, as well as its centre of power.
Down through the centuries Panzano was frequently to find itself embroiled in war. The recurrent controversies between Florence and the Siena guaranteed that Panzano, situated at the southernmost boundary of the Florentine State, stood at the centre of a "hot spot".
During the 15th century, Chianti suffered two disastrous invasions at the hands of the Aragonese. Panzano served as the last bastion of the Florentine defence. The castle itself was not badly damaged, but the surrounding countryside was apparently laid waste.
After the fall of the Sienese Republic in 1555, defence ceased to be of the highest priority. The fortifications were gradually dismantled and converted into farm buildings. The castle walls still stand around the entire perimeter of the fort and two of the original corner towers still stand. One serves as the bell tower for the parish church. The other, more imposing, is a private home.
The style of many architectural elements in the surviving structures leads us to date the construction of the castle in the 13th century. Later, a village grew up around the foot of the castle, and became the most visible part of the settlement.
Today as in the past, part of the area of the castle is occupied by the parish church of Santa Maria Assunta in Cielo. The church was built at the turn of the 19th and 20th centuries on the site of a former, late-medieval church building. It contains a few works of art salvaged from the previous building. Mass: every Sunday at 11.
Pieve di San Leolino
Coming on the SR 222 from Siena, about 1 km before Panzano, a little road to the right leads to the Pieve di San Leolino of Romanesque style but with an elegant 16th century portico.
The works of art are numerous: Madonna and Child with Saints, a 13th century altar frontal attributed to the Florentine painter Meliore di Jacopo, a 14th century Madonna and Child by the "Master of Panzano", and the wonderful triptych of the Madonna and Child with Saints painted by the Florentine Mariotto di Nardo in 1421.
The original church of San Leolino was presumably built at some time during the 8th or 9th century when the population of Chianti was beginning to organize into small villages or communities. A record of the year 982 contains the earliest reference to a village called Flacciano situated at the centre of the valley between Panzano and San Leolino.
During the 11th century San Leolino was rebuilt in Romanesque style. The basic structure consists of three naves divided by six arches. The ceiling of the central nave is crossed by beams. The church is nearly devoid of decorative elements except for the simple, rounded cornice at the top of the pilasters. A number of architectural additions were made at San Leolino during the 16th century: the façade received a coat of plaster and a portal framed in stone. A portico was built along the front of the church. An elegant campanile was added at the rear of the church. The single apse was substituted with a wide rectangular space. Other "modernizations" were made at the same period, but eliminated during the restorations of 1942-43.
Castello di Montefioralle - Greve in Chianti
The fortified hamlet with a sentinel's round with its few houses facing it, dominates one of the hills that overlook the Greve valley. At the top of the village, beside the ancient castle, there is the church of Santo Stefano with notable works of art: a Madonna Enthroned with Child of the late 13th century Florentine school, accompanied by a 15th century gold leaf panel with The Trinity and Saints attributed to Neri di Bicci.
Badia a Passignano
On the Senese road of Sambuca, you reach the splendid Badia a Passignano with its small centre, the tower house and the church of Saint Biagio with remains of frescos dated from the 500`s.
The Abbey, founded in 1049, became right away an imposing fortified monastery complex, including the church with a single nave. Inside are conserved frescos and important paintings, which include the frescos of the main chapel, by Domenico Cresti, nicknamed "Passignano" and the paintings of Saint Giovanni Gualberto to whom is dedicated the chapel. The monastery is still today occupied by the Valombrosiani monk community.
Volpaia
Volpaia was recorded for the first time in 1772 in a document. It was not until the first half of the XIV century however, when the castle became one of the main centres of the Lega del Chianti, the Chianti League in the Radda area. After the fall of the Sienese Republic the castle lose its purely defensive function.
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