Vertine, Meleto, Rietine, Castagnoli, Starda, Monte Luco della Beraredenga, Montecastelli

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The Chianti Castles route

La Strada dei Castelli del Chianti

Violet Itinerary - Vertine, Meleto, Rietine, Castagnoli, Starda, Monte Luco della Beraredenga, Montecastelli

After reaching the important crossroads of Molinlungo, you take the road to the left towards Radda. Almost at the beginning of this road, after a wonderful view on Vertine, another road on the right heads to San Piero in Avenano. This village was first mentioned in 995 and its title was transferred to the parish church of Spaltenna, then to the church of Gaiole. It is a very rare example of gothic country church with three large naves.

Castello di Meleto
Meleto Castle

If you take road on the right instead you will immediately see the Castle of Meleto on the crest, surrounded by centuries-old trees. It can be reached via a road on the same side. Not very much is known of the origins of Meleto castle. It was probably built at the end of the 12 C by a line of the Ricasoli family. It was occupied for a short time by the Sienese in 1478, but a further siege in 1529-30 was unsuccessful. The present building has an almost square outline that encloses an older tower. The two cylindrical towers on the southern and eastern corners where possibly built in the 15 C. The latter is very well preserved with a scarp wall base and machicolations at the top. The rest of the building, around a small, elegant courtyard in Renaissance style, was completely rebuilt during the Baroque period, as the corbelled windows and the massive portal in the south-western façade testify.

Continuing beyond Meleto, you go on climbing until you reach Rietine on the right. This is the site of a castle which is known to have been inhabited by a certain Azzo of the Ricasoli family in 1039, and the family continued to own it after that date. Nowadays no remains of the castle can be located. A bit further on, you find Castagnoli, a castle donated to the Abbey of Coltibuono in 1104. It is mentioned as "Castagno Aretino" in the Poggibonsi ruling in 1203 that delimited the frontiers between Siena and Florence. The Sienese besieged it unsuccessfully during the Aragonese war in 1478-79. The castle looks now like a mighty polygonal stone block with various rounded edges. There is a picturesque courtyard in the centre that can be accessed through a large arch in the southern part and a very narrow lane in the western part.


From Castagnoli you ascend eastwards on a beautiful panoramic road through a wooded region and, just before reaching Monteluco, on a road on the left, you go down to Starda, a picturesque village in a magnificent position.

When you reach the non-picturesque facilities of a TV repeater, take the path through the thick pine woods and climb to Monte Luco della Berardenga. This was one of the most important castles and the richest in history on this border area between Siena and Florence. It is mentioned for the first time in 1085 as a donation by the Berardenghi family to their Berardenga abbey. Although a part of it was donated to the Bishop of Siena at the beginning of the 12 C, it remained basically a property of the Berardenghi family. It was a frequent object of contention because of its position. In 1176 Siena had to surrender it to the Florentines and this was confirmed in 1203. However the Sienese reconquered it in 1261, destroyed it and obliged the Berardenghi family to sell it to them for 500 Liras. After a few years, the Florentines occupied it again, rebuilt it and, since then, this castle has given its name to one of the "terziere" (thirds) of the Chianti area. It achieved great importance due to its frontier position, even during the Aragonese wars. The Sienese, who managed to reoccupy it yet again in 1527, set fire to it and had it dismantled. Thereafter it was never rebuilt. Today only few remnants of wall and a cellar remaining amongst the woods.


Continuing on from Monteluco for some km on the road that descends to San Gusmè and Castelnuovo Berardenga and leaving it just before Capannelle for a forest road on the right, you reach Montecastelli, a castle of the Ricasoli family, known since 1203, and which revolted against the Florentine Republic in 1391. It was retaken by the Florentines, was conquered by the Sienese in 1432, who had to surrender it with the peace of Ferrara, but seized it again in 1478, and destroyed it. After that Florence took possession of it but never wanted to rebuild it. Nowadays many ruins in the wood and a tall stone wall with beautiful corbels remain.

Brown Itinerary - Pieve di Spaltenna, Vertine, Uliveta, S. Donato in Perano, Vistarenni
Red Itinerary - Tornano, Morelline, Cacchiano, Monte Lodoli
 - Gaiole, Barbischio, Capannelle, Cancelli, Castello di Montegrossi, Badia a Coltibuono
Violet Itinerary - Vertine, Meleto, Rietine, Castagnoli, Starda, Monte Luco della Beraredenga, Montecastelli
Orange Itinerary - Campi, San Sano, Monteluco di Lecchi, San Polo in Rosso, Galenda, Le Selve
Blue Itinerary - San Giusto a Rentennano (alle Monache), Lucignano, La Torricella, Castello di Brolio

Anna Maria Baldini

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