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The Chianti territory was the battle-field for the republic of Florence and Siena: not only because it was a borderland, but also because his geographic conformation made it was suitable for fortification: two real and proper defensive lines came to be created. Let us make a tour trough this castles:

the first castle that we find on the road from Radda to Gaiole is the SAN DONATO IN PERANO today it's changed in a big 17th century villa built on the fortified ruins (before 1000) that dominates the village.

Driving back to the SS 429 you reach the ruins that today can bee seen of the CASTELLO DI MONTEGROSSI. It was the sentinel and last rampart of the medieval feudal system constituted in the Chianti region. Erected at around 700 meters high on the crest of the last relief of the small mountain chain on the border between the territories of the Chianti and the Valdarno, perennial object of disputes between Florence and its enemies, the castle dominates the pass and the road that connects the two areas and also a big part of the valleys from both sides.
The first notices of the castle are of the year 1007 as a property of the two sons of Ridolfo, the origin of the families Firidolfi e Ricasoli. In 1172 it was conquered and destroyed by the Florentine that wanted to free their movements in the zone from a big obstacle. Some years later the rests of the castle belong to the Firidolfi family, that reconstructed it. They used Montegrossi also as base for actions of brigandage and looting of the caravans direct to Florence. Afterwards the castle made part of the chain of fortifications wanted by the Emperor Barbarossa to control central Tuscany. But during the war between the League of the Tuscan Communes and the imperial armies, the Florentines took again posses of the castle. Montegrossi was strengthened and was gifted of a permanent garrison.
In 1530 Charles V° that destroyed definitely the castle. Since then the ruins of Montegrossi were abandoned, but on the crest of the mountain still rises the mighty keep surrounded by the walls, unfortunately only shed stones in the vegetation, of the fortified enclosure.

Near the vilage of Gaiole there is the castle of BARBISCHIO: under Florence, it had a wall with three towers. In the 1049 it was presented to the monks of Coltibuono, and in the 1220 it became a feud of the Conti Guidi until it felt into the hands of the Ricasoli Family. At the end of the 15th century it was detroyed by the aragonesi. The tower has been restored.

Of interest is also VERTINE, The "walled town" was the biggest Castle of Chianti region. In the 13th century it belong to the Ricasoli Family. Because Vertine was never at the centre of war events as sieges or fighting, it reached us quite intact. Only in the 15th century its fortifications were restored and enlarged. On the southern front rises a splendid rectangular tower that had the function of keep.
On the left side of the keep there is the north gate, once twin of the opposite partially disappeared south gate, still today the only two entries of the suburb. The arch of the south gate is lost but we are still able to notice the tower that defended it.

On the SS408 from Gaiole to Castelnuovo we find the little road that drive us to the CASTELLO DI MELETO: built in the 11th century it belong to the Count Ugo, Marchise of Tuscia, later it was presented to the monks of the near Coltibuono Abbey. The name of the first vassal of the castle was Guardellotto. This was stripped of all his possessions for some contrasts born with the Emperor Federico Barbarossa that entrusted Meleto to the local family of the Firidolfi.
Its strategic position made of this castle one of the principal fortifications of the Terziere (one of the three parts in which these Florentine military organization was organized) of the 'Chianti League' headed by Gaiole. It was for centuries theatre of wars but it has never been destroyed. The 'military' destination can be seen also today: the form of irregular quadrate, almost a trapeze, with the presence at the centre of the keep, although notably lowered, show us a classical example of castle- enclosure.
In 1478 the castle was occupied by the Aragonese army allied with Siena, two years later it was quickly regained by the Florentine that started great works of reinforcement of the structures.
The 1480's addition is today practically still intact and consist in the two mighty cylindrical bastionated towers, gifted of machicolulis (opening between corbels of a parapet through which the defenders can drop rocks or fire projectiles against an enemy directly below them) posted at the two southern angles (the more exposed); of two hoarding in bricks at the northern angles overlooking the border of the crag, so already naturally defended; the reinforcement of the walls curtains toward the only road of access and the insertion of loopholes and gun holes, partly disappeared, along the perimeter of the enclosure. Thanks to this in the 1529 Meleto victoriously withstand to the siege of the imperial troops. The Meleto castle was transformed in a villa during the 18th century and its defenses were partly dismantled. The interior, visible by a fee, has still today the aspect of this period, with decorated halls and a particular little theatre of the year 1742 still provided of its seven original scenographies. Meleto remained ownership of the Ricasoli family until about thirty years ago, today is center of an agricultural firm for wines production.

On the same road we find also the CASTELLO DI TORNANO: built in the 11th century it belong to the noble from Siena Guarnellotto dei Mezzolombardi until the 1167 as he rebelled and the Emperor Friedrich the 1rs gave him to Ranieri de' Firidolfi Ricasoli. It’s known that Guarnellotto, thanks to Siena, maintaned the control over Tornano and over the nearby Castle of Campi.
In 1400 Tornano was fortified by the Ricasoli and during the invasions of the aragonesi it succeeded to keep on until 1530 as it was conquered by the emperor armies.
The castle was recently restored and today is an agriturismo with a farm.

Driving back an taking the road SS 484 you will arrive to the CASTELLO DI BROLIO It has a Longobard origin, that is revealed only by its location. At the beginning of the 12th century the family of the Ricasoli from Cacchiano took office on it and today the castle belongs still to their descendants.
Its position was always strategical for the control of this area of Chianti, from the 1176 it was edge of the Florentine influence at the borders with the Senese territory. For this reason, since the 13th up to the mid 16th century, the castle was often interested in the frontier wars. Siena tryed more times in conquering the castle, until the second aragonese occupation when it felt into Siena’s hands, but only until 1484 when the castle returned Florentine, began a great work of restructuring and expansion of the fortification to adeguat the walls at the new fire weapons, so we can consider Brolio one of the first 'Italian bastioned fortresses' (the architect was Giuliano da Sangallo).
During the siege of Florence (1529) the castle was again occupied and parts burnt. The next year Florence conquered it again.
This bastioned walls enclose the rests of the original medieval castle, above all the keep and the Roman Chapel, over that a neo-gothic building was build to the place of the preexisting one from the Baron Bettino Ricasoli, 1809- 1880, famous political man of the last century, known also as the 'Iron Baron'.
Inside the Baron let make an interesting archive of Renaissance works: it can be visited the lunch-hall, hung with tapestry of Flemish school, armours and a big iron chandelier decorated with the coats-of-arms of Ricasoli and the original appartament of Bettino Ricasoli. The Chapel of San Jacopo can also be visited (1348). The facade is decorated with a modern mosaic and there are a polyptyc with Virgin Mary and the Saints of Ugolino di Nerio (14th century.); the Crist’s Predication and the Adulteress, mosaics made by Augusto Castellani over paper of Alessandro Franchi. Behind the altar a stairs bring in the crypt, where there are the Ricasoli family’s tombs.

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