Castellina in Chianti, Tuscany

Castellina in Chianti is a sight to behold!

After passing through endless rows of ilex and cypress trees in the San’t Agnese wood and nature reserve, being greeted by this medieval town of Castellina in Chianti sitting atop a hill is simply hypnotic and a feast for the eyes.

Castellina was an important fortress of Florence in ancient times, and today continues to be an important center of wine and olive production in the Chianti. Its crenellated tower and castle-keep that has outlived the passage of time, is proof to the important role that this town played in its tumultous history.

The medieval town square has changed very little since it was laid out during the 15th century, even with the introduction of modern amenities, that make this town a a favorite holiday destination among British and Europeans travelers.

Castellina in Chianti, Tuscany

The influx of tourist and new money into this town has done it some good. Old buildings, many dating back to the era of the grand dukes, have been restored. The flip side is that many of these are now holiday residences that are not available to the public.


Castellina in Chianti is an attraction in itself. It has traces of the ancient Etruscan civilization as evidenced by the four Etruscan tombs dating back to the 6th century that has recently been uncovered and yielded interesting finds.

The Rocca Comunale now serves as the town hall and houses a small Etruscan museum, from the nearby four Etruscan tombs at Monte Calvario.

The Church of San Salvatore is a neo-Romanesque 16th century church. A fresco of the enthroned Maddona can be viewed here, as well as some other important religious relics.

Via delle Volte is a very impressive arched passage leading along the eastern wall of the town. The private dwellings on top of the wall are later additions, when the original purpose of the arched passage has become irrelevant in present times.

The Church of Sant’Agnese with its imposing bell tower at the main road from Castellina in Chianti to Poggibonsi.

The ruins of the Castle of Monternano is a very charming spot, but very difficult to find as it is covered with wild vegetation. Only the doors, arches, walls, and underground passages are still visible. For the very curious spirit.

Wine Festival

The wine festival is held during the last week of September (Sept. 22-23, 2007), when it is possible to sample wines, Tuscan food, and witness the parade. If you miss this festival, you can buy wines at the Melini Wine House, (established in 1705) at the west side of SS429 towards Granaio, or at Bottega del Vino Gallo at Via della Rocca 10.

Nearby Villages

San Gimignano is not to be missed in any Chianti driving tour, or visit. It is a charming, medieval town, with soaring towers, and is a favorite of a very well-known British royalty.