One arrives in Castellina after ascending for about 7 or 8 kilometres to 595 metres above sea level. The Chiantigiano town is set on top a hill overlooking an expansive view of the Elsa Valley. Beyond the valley the Metallifere hills can be seen impeding the view of the Mediterranean (the Tirreno sea).

Castellina, like most Chianti villages has its origins as a military outpost and wasconstantly passed from hand to hand in the course of history between Siena and Florence. In evidence today the antique medieval tower, and, as a reminder of even more remote history the Etruscan battlements of great importance.

From Castellina one can descend into the Valley of Elsa and drive upwards to SAN GIMIGNANO (the town of towers) or another road towards the fortress of MONTERRIGIONI, and Dante's "round circle" and on towards SIENA which is only ashort distance away. Taking yet another road in the opposite direction leads instead to RADDA IN CHIANTI.

The Chianti wine region is a gorgeous part of Tuscany and Castellina in Chianti remains one of the most evocative medieval towns in the Chianti terrority. 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 Castellina makes it an ideal starting point for day trips to surrounding towns and cities like: VOLTERRA, RADDA, GREVE, FLORENCE, CORTONA, AREZZO, SIENA and MONTALCINO among many others.

The first historical evidence of Castellina starts with an Etruscan group of dwellings set on the slopes of SALIVOLPI here today we can see a crafted well and the remains of the surrounding walls of the dwelling. Nearby, the etruscan burying place at MONTE CALVARIO, four tombs set in a cross after the cardinal points, which gave great importance to the site in the Vll and Vl centuries A.C. Of relevant importance also is the Necropoli of POGGINO in the FONTERUTOLI area brought to light only recently by a local group of archaeologists. The village of Castellina itself in its present location has probable Roman origins, but sadly traces of these origins have been lost over the centuries until Castellina's importance as a strategic military position was recognised in medieval times. History speaks about the Trebbiesi Castellina in the Xl century, Trebbio being the name of a nobile family from the court of Conti Guidi, landlords of a nearby castle of which the remains can be seen at BADIOLA.

In the Xll century Castellina became an important military garrison for the Florentine military, situated as it was on the boundary between the states of Florence and Siena. It became the Principle centre of the ancient league of Chianti with RADDA and GAIOLI. Later in the XlV and XV centuries it was the theatre of raids and lootings by the state of Siena. These raids forced the Florentines to have to rebuild and strengthen the surrounding walls, work carried out by the famous architect Filippo Brunelleschi.

In 1478, while Florence was at war because of the "Mad conspiracy", Giuliano da Sangallo was summoned to Castellina to restrengthen the defences. Of this episode there is a complete account in the "Lives of Vasari". Baldassar Castiglione in his "Cortegiano" tells instead of a siege that lasted 40 days, led by the Duke of Calabria, a sworn enemy who used weapons of those times in the form of bombardments with catapults and medicate dmissiles capable of causing epidemics and plague.

In 1483, after the Florentine war, Castellina returned to the Medici of Florence and in the XVI century lost its military importance. The war between Siena and Florence ceased and both became unified as part of the Tuscan territory under Cosimo I of the Medici, who transformed the military outpost into a rural farming and sharecropping center.

In 1865 the Castellina municipality was formed and was later transferred in 1927 to therestored medieval tower in the Piazza del comune. The second world war saw Castellina once again torn by war and the passing fronts. The bombardments destroyed the ancient Florentine door at the north end of Via Ferruccio and the adjacent parish church was seriously damaged. The facades and bell tower were later rebuilt after the conflict was over.