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Castellina in Chianti by Rhett

Welcome to Castellina in Chianti
from Jesse's Journeys in Italy

Population: 2,820 (2004)
Official website:
Castellina in Chianti
Wikipedia: Castellina in Chianti

The Chianti wine region is a gorgeous part of Tuscany, and Castellina in Chianti is one of its most evocative medieval towns in the Chianti territory. With incredible views, intimate piazzas and some wonderful restaurants, boutiques and art galleries, Castellina makes a perfect base for a holiday in Tuscany.

While the town itself is beautiful, the geographic position of the town is also ideal for day trips to surrounding towns like Volterra, Radda, Greve, Cortona, Arrezzo, Siena and Montalcino among many others. 

More so than some of the other towns in the region however, Castellina seems to have more going on, in terms of night life and festivities. There are some quaint lounges and locals which make an ideal place to enjoy a typical Italian "aperitivo" before the dinner hour and some well known Tuscan artisans and artists who display their work here regularly.  

Whether you are considering renting a villa near the town, or staying for a few days in any number of gorgeous hotels in the area, we think that Castellina is at the top of places to stop at and hopefully to stay during your vacation. 

Well situated between
Florence to the north and Siena to the south, the town sits on a dramatic rise of ground between the Pesa and Stagia rivers, a position which once gave it strategic command of the roads passing from Etruscan settlements like Vulci, Vetulonia and Roselle on the coast to the west and the market towns of the north, as well as the much traveled routes to the Adriatic, particularly to the harbour at ancient Spina.

The town may have been inhabited before the area was dominated by the Etruscans, but most historians place its founding to as early as the 7th century BC.  At Mount Calvario outside the town on the road to Florence, there is an Etruscan burial vault about  53 meters in diameter that testifies to these ancient origins.  Mount Calvario was once an important point for another reason - serving as the last station  on a medieval "Ways of the Cross" pilgrimage route.  Apparently a small chapel once sat on its peak, its priests and parishioners quite unaware of the graves below.  There is also an Etruscan necropolis on the road toward Siena (at Poggino, near the hamlet of Fonterutoli) containing 5 tombs and another chamber of uncertain use dating to the 6th century BC - when the Etruscan civilization reached its apogee.

The subsequent history of Castellina follows the usual pattern of the area.  It continued as a semi-important settlement in Roman times and suffered numerous tribulations  including almost total destruction by fire sometime around the 1st century BC.  The town eventually came back to life and found itself immersed in the conflicts that characterize the long decline of Rome, and the even longer medieval period.  Situated in the middle of much stronger towns and cities like Volterra, Chiusi and Fiesole, Castellina in Chianti, found itself drawn into innumerable conflicts with the usual sad results.

In the late middle ages, the town was a member of the Chianti Alliance along with several other towns in the area, a sometimes successful effort to defend, variously, against the predations of the Sienese and Florentines.  Castellina's position commanding the areas' important roads and the Val d'Elsa gave it a strong military role within the alliance.  At this time, early in the 15th century, a formidable and severely architected castle, La Rocca, was built along with defensive walls containing  well-spaced towers.

The Rocca still stands, serving now as the sleepy town hall and as a museum, as do many stretches of the walls.  The museum's collection includes ornaments and parts of weapons made of iron and bronze,  Etruscan-Corinthian ointment jars made in Vulci, other vases made of vitreous paste, and two Attic vases painted with black figure.

The original walls featured only two gates, one opening to the road to Siena and the other to the road to Florence.  Both were destroyed in actions during WW II.  They stood, however, through a long, destructive sequence of battles and sieges in the Middle Ages.  In 1397, the town was stormed, occupied and mostly destroyed by Alberico da Barbiano, Duke of Milan.  In 1452, troops under Ferdinand of Aragon tried the same thing but was turned back.  Once the town came under the domination of Florence under the Medicis, the town walls and other defenses were fortified by the famed architect Giuliano da Sangallo, but these proved ineffective when, in 1478, the town was attacked by the Duke of Calabria.

Things settled down after Florence re-asserted control, and the town's history since has been essentially peaceful, although its economy, which once depended on its strategic location, declined.  Castellina now survives on a local agricultural production and, of course, tourism.

Indeed, as one of the principal towns in the Chianti, Castellina is a place where one can find and sample an array of wonderful wines and olive oils.  Visitors can stay nearby, at one of our favourite places, the Hotel Villa Casalecchi, and enjoy the town and its surrounding area for a few days. Or, one can simply come for a few hours to enjoy the sites, and tuck in for a lunch or dinner of traditional Tuscan cooking at one of the town's busy restaurants.

Of interest in and near Castellina in Chianti:

  • Rocca Comunale - 15th century - the town hall and museum with an impressive atrium, once the Captain's Hall.  Ascend to the top floor for a spectacular view of the town and surrounding landscape.
  • Via delle Volte - an impressively arched passageway along the eastern walls.  Originally open, it is now a vaulted "tunnel" formed when various structures were built above.
  • Palazzo Ugolini -  formerly Palazzo Squarcialupi - its wide facade, featuring three ashlar doors, bears the coat of arms of the Ugolini.  Note the eight arched windows on the primo piano - the first floor above the main floor.
  • Palazzo Biancardi - three stories with two tiers of sandstone framed windows. Above the entrance is the Medici coat-of-arms of Pope Leo X (Giovanni de Medici, son of Lorenzo il Magnifico and pope from 1513 to 1521) who stayed here when passing through in 1513. 
  • Chiesa San Salvatore - 16th century - neo Romanesque - mostly destroyed in WWII, but rebuilt.  Contains a staccato fresco of the Madonna attributed to Bicci di Lorenzo and a wooden statue of San Barnabas, the town's one-time patron saint.  The present patron saint is San Faustus, and the church has a gold urn purportedly containing his remains.  Other objects include works from the 15th, 16th and 17th century.  The massive organ dates only to 1965.

Other points of interest near Castellina in Chianti include:

  • Fonterutoli - This town, which takes its name from the Latin fons rutilus (clear spring), lies on the road leading from Castellina to Siena. The ancient castle stands on a hill overlooking the Elsa valley, on the border between the municipalities of Siena and Florence and the dioceses of Siena and Fiesole. Reference to it is made in a diploma by Pope Alexander III in 1177. The church, dedicated to San Miniato, was the site of important agreements between Siena and Florence, such as the one signed on 29 March 1201 that granted Siena the right to annex Montalcino and the one signed on 6th October 1208 whereby Siena renounced its right to Poggibonsi and all its territory. Unfortunately very little is left of the original church and the castle.
  • Conio - boasts an ancient Romanesque parish church, San Leonino, with a quite beautiful interior and charming, but small cloister.  The adjacent buildings once served as residences for the priest.
  • Sant’Agnese - another old parish church of Sant’Agnese with its imposing campanile (bell tower), on the main road from Castellina in Chianti to Poggibonsi.
  • Cispiano - Here there are imposing ruins of Monternano castle, whose origins date to 1089 AD.  The castle was destroyed in 1254 by Florentine troops and the ruins are covered with wild vegetation though one can find doors, arches, walls and underground passages in the midst of the green chaos.
  • Rencine - overlooking the fortress of Monteriggioni in the southern part of the area.  Here you can find the ruins of another immense but almost completely destroyed castle.  The church of San Michele, however, stands in a state of good repair.

Region of Tuscany



Florence - 66 km
Greve - 20 km
Siena - 23 km
Arezzo - 70 km
Pisa - 105 km
Lucca - 130 km
Lerici - 193 km
Monterosso Al Mare - 240 km
Rome - 257 km




Coat of Arms for Castellina in Chianti