The Chiantigiana or SR 222 is a road that takes you around the entire Chianti area, from Florence to Siena. Our journey starts from Florence, passing from Greve in Chianti, Panzano, Castellina, Radda, Gaiole and finally Siena for a total length of 69 kilometres.
From Florence we take the SS 222 road in the direction of Greve in Chianti, along a route that offers beautiful views of hills, vineyards, olive groves, villages and castles.
Greve in Chianti is considered to be the gateway to the Chianti region for those travelling south from Florence. In the past, Etruscans and then Romans inhabited the area, while the actual town centre dates back to the Middle Ages. The town had a favourable location at the crossroads of major pilgrimage routes (Via Francigena and Via Volterrana) and this favoured its development.
In Greve in Chianti, the main square is Piazza Matteotti with the monument of Giovanni da Verrazzano, the arcades and the typical structure of ancient markets, symbol of the important commercial role of Greve. Here you can find also the Town Hall in neo-Renaissance style and the Church of Santa Croce, built on the ruins of the medieval church.
Other curiosities about Greve: it is the birthplace of the navigator Giovanni da Verrazzano who discovered the bay of New York. Here you can find the famous Castello di Verrazzano with renowned wine cellars offering a daily visit and wine tasting; there is also a Wine Museum where you can taste over 100 types of wine.
From Greve two roads start: one leading to the valley of the Arno near Figline and S. Giovanni; the other is narrow, winding and partly unpaved and connects to the Via Cassia near Sambuca Val di Pesa through the enchanting villages of Montefioralle and Badia a Passignano.
Continuing along the Chiantigiana road you find Panzano, part of the municipality of Greve in Chianti.
The oldest and highest building of Panzano is the castle, with well-preserved surrounding walls. It has a single gateway and through a single road we arrive at a small square on which stands the Cassero, composed of a high tower that rises higher than all other buildings. Just outside the castle there was the ancient church of Santa Maria, replaced by the current one in the late 19th century. The castle and an ancient village are currently known as Panzano Alto, made of two parallel roads that join the square to the castle.
There are two ancient and charming churches near Panzano: the Parish Church of San Leolino and the Oratory of Saint Euphrosynus, both of which are worth a visit.
Panzano in Chianti is also well-known for two fairs - Vino al Vino, a wine festival held on the third weekend in September, and the Festa della Stagion Buona held on 25 April.
It's also home to a well-known butcher and enthusiast for bistecca alla fiorentina (Florentine beefsteak), Dario Cecchini.
Continuing on our journey we arrive at a crossroads: if we go straight ahead we reach Castellina in Chianti after 20 kilometres. If we turn left, we reach Radda in Chianti.
Castellina in Chianti was born as a military outpost, repeatedly contested between Siena and Florence. The ancient medieval fortress and an impressive hexagonal wall still visible today are evidence of the struggle between the two cities. The wall was destroyed and rebuilt many times and legend has it that even Brunelleschi was asked to work on the project of building new walls for the town.
Today Castellina is an important centre on the Chiantigiana road with large forests and rich fauna all around.
Here you can visit the neo-Romanesque church of San Salvatore just outside the town and Montecalvario, a burial complex consisting of four ancient Etruscan underground tombs. Outside the city centre, there is also the Fortress with its tall tower to be visited: it offers, in fact, a stunning panorama of the town and countryside. The Fortress is also the Town Hall and houses the Archeological Museum of Chianti.
The most characteristic street of Castellina is the medieval Via delle Volte, once an impressive underground tunnel used by the guards, now a covered street with shops and restaurants.
Castellina is also the place where in 1924 the Chianti Classico Consortium was born, and since 1984 it has the DOCG mark. Read more about Castellina here.
From Castellina you can go down to the Elsa Valley and back to San Gimignano and Monteriggioni or, alternatively, in a short time you’ll reach Siena through Fonterutoli. Let's take a detour from the SR 222 and head to Radda in Chianti.
Radda in Chianti is a delightful medieval town enclosed in large defensive walls that still maintain their medieval look.
Coming from Castellina, you immediately notice the crenelated tower and houses all around. Radda was the ancient capital of the League of Chianti, and today still has a historical importance for wine tradition.
The Romanesque Church of San Niccolò located in the main square characterises the village. You can also visit the Grand Duke’s Ice House, or the Museum of Sacred Art of Chianti located in the Franciscan Convent of Santa Maria in Prato.
In Radda’s surrounding countryside it is also possible to visit the parish of Santa Maria Novella as well as numerous castles and fortified medieval residences.
Back on the Chiantigiana road again you can continue for about 10 kilometres and arrive in Gaiole in Chianti.
The history of Gaiole in Chianti is linked to its position on crossroads used for communication between the Chianti and the Valdarno, and Gaiole became the seat of the market for the nearby castles. Since it was a marketplace, it didn’t need walls or fortification and its centre was destroyed and rebuilt many times, so few buildings have been preserved. It is an important city within the Chianti Classico region and the main attractions are the wineries in its surroundings, some beautiful castles and parish churches.
You can visit Cacchiano Castle, built in the 13th century by the Ricasoli family; Brolio Castle, renovated by the famous architect Sangallo; and Monteluco Castle on a hilltop just a few kilometres from Gaiole. You can also visit the Parish Church of Spaltenna with a valuable 15th century crucifix; the Castle of Vertine, a small medieval walled village; and the Abbey of Coltibuono, a former monastery now turned into a wine estate.
Next stop along the Chiantigiana road is Siena, and with this city our journey comes to an end.