The region of Tuscany that is today Castellina in Chianti was largely uninhabited until the early Etruscan period, when these first settlers to the boot of Italy made their way to the site of the modern town. Even in those days the settlement was likely faced raids from Gaul.

By the 7th and 6th centuries the power of the Etruscans passed to the Romans, and within the next 100 years much of the territory around Castellina in Chianti was part of the Roman Republic, and later the Roman Empire. The town of Castellina remained a link in the various trade routes of Italy, and this continued even after the fall of the Roman Empire.

During the Middle Ages control of Tuscany passed through various rules, and fearing outside attack Castellina in Chianti was largely fortified, and today is an outstanding example of this early Medieval style of architecture. The city was the site of several minor battles in structures between Florence and other Italian states, and under the Medici family became part of the power Republic of Florence. It was later controlled by the Habsburgs of Austria, by the Emperor Napoleon and in 1861 became part of the unified Italy.

The town of Castellina in Chianti survived two World Wars, although the surviving early Renaissance city gate was destroyed. Today the city remains a fantastic example of a walled Italy town, complete with buildings that endured through the ages.