The next time you’re driving along the old ‘Strada Chiantigiana’ road now known as the Strada Regionale 222 (SR222),  take a moment to stop admiring the breathtaking Tuscan landscape and explore the charming town of Castellina in Chianti.  Offering a long history reaching back to the Bronze age, the city’s origins go back to Etruscan times that you can still explore today at the nearby archaeological sites and in the Archeological Museum located in the city centre. The Etruscan site of Monte Calvario is just outside of town and can be easily visited too.

This is one of the most important towns in the Chianti region and home to some fascinating architectural features.

In the mid-1200’s the “Lega di Chianti” was formed as a governing body comprising the towns,  Castellina, Radda and Gaiole.  Castellina would become a major stronghold in Florence’s defensive system against Siena due to its high position and in fact, the growth of Castellina is historically linked to the Florentine conquest of the Chianti region.

The powerful cities of Florence and Siena fought many historic battles and are responsible for the destruction and rebuilding of Castellina many times.  In the early 15th Century, Florence decided to improve its southern borders,  and so built the fortress and tower, known as ‘La Rocca’.    

When Siena besieged Castellina for 44 days in 1452, the fortification resisted and much of the surrounding wall still survives. Square cut-off towers can be seen to the east and the gate and windows in the west front of the tower presumably belong to the original stone building, whilst all the rest is a later reconstruction, incorporated into the modern architecture. Every time the town was reconstructed, bigger defensive walls were made.  Legend tells that the great Brunelleschi was even asked to work on the new walls for the town.

The quadrilateral shape of the ancient medieval fortification has been preserved in Castellina in Chianti and the Rocca and its huge 14th-century tower have a magnificent view over the town and the surrounding Tuscan landscape.

Part of the castle is now used for local government and part for the Archaeology Museum of Chianti Senese. The museum was originally founded because of the important artefacts discovered at the nearby Etruscan site of Monte Calvario.

One of the most interesting and unusual features you will find in Castellina is found under the ancient walls.  Known as the ‘Via Della Volte’, this impressive underground tunnel was once an open-air road before being built over when the city felt the need to expand.  Today it is lined with specialty boutiques, artisans and restaurants. The tunnel wraps around the city, and in the hot Summer months provides a welcome, cool and refreshing escape from hot sun.

The main street of Castellina is Via Ferruccio where you can find more local trattorias, cafes, boutiques and an amazing butcher named Riccardo Stiaccini who apart from selling excellent local meat, also provides a pretty delicious menu for a quick and convenient lunch.  After lunch stop by some of the other important buildings in the street, such as Palazzo Banciardi and Palazzo Squarcialupi and you will also pass the Church of San Salvatore. The church actually looks quite new because it was heavily damaged in the Second World War and  was rebuilt in 1945. Step inside the church however and you will find a 15th-Century fresco from the Renaissance of the Virgin and Child by Lorenzo Bicci.

Eat here :

MACELLERIA STIACCINI

Via Ferruccio, 33

Tel : +39 0577 740 558

ANTICA TRATTORIA LA TORRE

Piazza del Comune

Tel : +39 0577 740 236

OSTERIA IL RE GALLO

Via Toscana 1

Tel : +39 0577 742 000