For the Sienese side of Chianti we can start from Siena and from here with SR 222 reach Castellina in Chianti, otherwise continuing the itinerary of Florentine Chianti, from San Donato in Poggio, we reach Castellina in Chianti.
Castellina in Chianti by heading towards Poggibonsi and taking the S.S. 429 state road, exceptionally panoramic in this stretch. A short detour brings us to the ancient parish church of Sant`Agnese, skilfully renovated after being partially destroyed by cannon fire during the last war. Castellina in Chianti is set in a splendid hilltop position between the valleys of the Arbia, the Elsa and the Pesa. With a municipal territory entirely comprised within the Chianti Classico area, it is one of the most important towns in Chianti and a constantly developing holiday resort. Of Etruscan and Roman origins, it was a feud of the nobles of Trebbio in the eleventh century, it then became an important Florentine military garrison. Together with Radda and Gaiole, it was part of the Chianti League in the thirteenth century. Subsequently, in the fourteenth and fifteenth centuries, Castellina was subject to raids and sacking, and was provided with walls by the Florentines between 1400 and 1402.
Dominated by the historic Rocca, or fortress, composed of an extremely high defensive fort (surmounted by an even more imposing keep) the town features fortifications and mediaeval sections, such as the suggestive Via delle Volte, and partially preserves its fifteenth-sixteenth century character. In the surroundings are many farmhouses dating to the grand-ducal period and even earlier. Not far from the centre of Castellina is a large Etruscan tomb dating to the fourth century BC, the Tumulo of Montecalvario, this is one of the most interesting discoveries of local archaeology, bearing witness to the very ancient human presence in the Chianti region.
The churches in the surroundings are numerous, and all nteresting Particularly well worth visiting are those of San Martino a Cispiano, single-aisled with a fine apse, which has preserved all its Romanesque grace, and that of di San Leonmo in Conio, which houses a Madonna and Child by Lorenzo di Bicci. Near the village of Fonterutoli is the Necropolis of Poggino with the remains of some Etruscan tombs.
In the southern part of Chianti 20 km from Siena, we come to Castelnuovo Berardenga, the name of which recalls its origins as a fortified hamlet. It is set on a hilltop between the Ombrone river and the Malena torrent, in an area traditionally devoted to agriculture and where the economy still hinges of the production of wine alongside the craft-working of wrought iron. The castle (the last to be built in the area, of which sparse ruins and one tower remain) was constructed in 1366 by the Siena Comune with the intention of giving Castelnuovo a role of pre-eminence over the territory of the Berardenga. In the town is Villa Chigi Saracini, surrounded by a fine park. In the environs, in Pacina, the parish church of Santa Maria Maddalena is particularly remarkable, of mediaeval origins with later modifications.
Also extremely suggestive is the small fortified village of San Gusmè featuring two of the original long-arched stone gates. Set in a delightful hilly area in the centre of a smiling valley, we come to Vagliagli, with the adjacent castle of Aiola. Also within the municipal area is the imposing Certosa di Pontignano, founded in 1343 and rebuilt in the second half of the sixteenth century. Previously the property of the Camaldoli monks, the charterhouse is now the premises of a University college and is used for scientific conferences and conventions. Well worth a visit is the hill of Montaperti, site of the bloody battle fought here on 4 September 1260, during which Siena conquered Florence where a stone tablet surrounded by a lovely ring of cypresses recalls the slaughter which, in Dante`s words, “made the Arbia run red”, (Dante Alighieri, Inferno, X, 85-86).
Heading northwards again, we come to Gaiole in Chianti. a wine centre and holiday resort surrounded by densely cultivated green hills. It grew up as a market town in the mid thirteenth century, when along with Radda and Casteilina it came to form the Chianti League. A little to the west of the residential centre, amidst woods and vineyards, stand two fortified mediaeval complexes: the parish church of Santa Maria a Spaltenna (first half of the twelfth century) and the hamlet of Vertine, recorded from the tenth century, enclosed within oval perimeter walls with an entrance gate guarded by an elegant tall tower.
One of the major attractions of the entire Chianti area is the Castle of Brolio. Now the site of one of the most important wine estates of the area, it is one of the first examples in Tuscany of a castle fortified with bastions. Built over a pre-existing structure by the Florentines after 1484, it features a massive polygonal enclosure surrounding the vast Romantic-style mansion built in 1860 by the architect Marchetti for Baron Bettino Ricasoli. There are also other fine castles in the area, such as Meleto and Cacchiano. The former, fortified probably in the twelfth century and trasformated into a villa-estate in the eighteenth, retains and contains an elegant little theatre, while the latter is a thirteen-century fortified hamiet which also forms part of the Ricasoli possessions. Enchantingly atmospheric is the ancient Badia a Coltibuono, founded in 1049; belonging at length to the Benedictines, it too has now been transformed into a villa-estate. Among the many churches, particularly well worth visiting are those of San Giusto in Salcio and San Polo in Rosso.
The proposed itinerary now reaches the last municipality of Chianti Radda in Chianti set on a hill which marks the watershed between the valleys of the Pesa and the Arbia. Now a predominantly agricultural centre (wine production) Radda boasts an ancient history. It passed from the hands of the Guidi counts to Florence in 1203, was equipped with fortifications in 1400 and later (from 1415) became one of the members of the Chianti League along with Casteilina and Gaiole; in 1478 it suffered argescale destruction at the hands of the Pontifical troops of the duke of Calabria. The town preserves traces of the walls and towers of the ancient fortifications, as well as the mediaeval urban layout on an elongated elliptical plan. In the centre of the town, the facade of the Palazzo del Podesta is emblazoned with noble coats-of-arms. Rebuilt in the seventeenth century, the Franciscan convent of Santa Maria al Prato is destined to become the premises of a museum of religious art housing works originating from the churches of Radda and Gaiole.
Not far from Radda, following the higher of the two roads which lead to Panzano, we come to the village of Volpaia, a fortified hamlet of mediaeval origins. The castle of the same name was built, probably around the tenth century, on the frontier between Siena and Florence Set in a highly strategic position, guarding the Pesa valley, the castle undoubtedly played an extremely important defensive role. The fortified complex has by now lost part of its walls, but still preserves a fine keep set in the centre of a small courtyard, and above all, a good number of renovated mediaeval dwellings. Within the walls there is also the church of Volpaia, still recognisable. Nevertheless, the most important building is the Commenda di S. Eufrosino, of fifteenth-century layout, dedicated to the bishop saint of oriental origins who is traditionally believed to have brought the Gospel to Chianti It is now used for art exhibitions and other events. Not far from Volpaia, immersed in a well-tended countryside, is the Romanesque parish church of Santa Maria Novella which played an extremely important role in the past. Of considerable interest, in the interior, are the Pre-Romanesque capitals with zoomorphic figures, of a kind rarely found in the Chianti area.