Enjoy Tuscany: Art, Culture and Tourism in Siena and Sienese Province.
Castellina in Chianti by Bicycle
By "Gli Amici della
Bicicletta"
via Campansi 32, 53100 Siena, Italy
tel. 0039-577-40137 (Fabio Masotti).
From Fabio Masotti’s book: "Chianti by Bicycle", Editrice Grafica L’Etruria
Castellina in Chianti - Castellina
Scalo - Monteriggioni -
Badesse - Lornano - Fonterutoli - Castellina in Chianti
Medium difficulty itinerary with 3 km of unmade road.
In the approach to Castellina in Chianti from the 429 or from the ss 22 there are two constructions which stand out above all the others: the fortress, a symbol of the medieval system of defence, and the Nicolai factory which is an extremely ugly work of architecture. Unfortunately it is the latter which is most noticeable from afar and it seems to soffocate and crush the rest of the town. Despite this the centre of Castelllina situated in an evocative position overlooking the valleys which descend to Val d’Arbia and towards Siena, is an important stage in a journey through the Sienese Chianti area. The history of the site is undoubtedly ancient; there is evidence of an important Etruscan centre since archeological digs have brought to light a tomb on the rise behind the present inhabited area. Apart from this the urban structure also takes us back to its medieval past when Castellina was the leader of one of the three "terzieri" into which the Lega del Chianti, the Florentine defensive system with a clear anti-Sienese function, was divided. Thus after the Lodo di Poggibonsi of 1023 which established recignition of the temporary supremacy of Florence over the area that Castellina became one of the furthest strongholds of the Florentine republic in the direction of Siena. It was sacked and rebuilt wifh new fortifications, passed into Sienese hands more than once only to return finally in 1483 under Florentine dominion. The present day walled town still conserves some of the characteristics of the thirteenth century fortifications; the walls are well preserved on the northern side and have several towers along their length. The rocca which stands outside the western wall was restored in 1927 and houses the Town Hall. The entrance and some of the windows are authentic whereas the rest including the battlements is the fruit of restoration work.
The itinerary begins in the centre of the town. Take the Siena road, the 222, and after a few hundred meters just in front of the Niccolai buildings take a right turn towards Castellina Scalo. Before starting the ride down it is worth stopping to take in the view which stretches out over the Val d’Elsa and the slopes gently extending down to the narrow plain. The road surface is good and there is littletraffic so the descent can be made without any particular risks and lasts about two km. Then there is a left hand turn leading to Castello La Leccia, which has been turned into a villa; early documentation, around 1077, records that a share in it was bought by the nobleman Rodolfo di Guinizio; it changed hands many times and suffered extensive damage during the wars in 1400-1500.
Once back on the tarmac you carry on down for another couple of kilometers until you get to the ancient medieval hamlet of Rocca delle Macie which is today a big vineyard and wich has a good view over the Castello La Leccia. Carry on for a few more Kilometers until the road becomes flatter and you see a sign for "Fattoria Lilliano", where a narrow track leads you steeply up for about 500 m. to the house and hamlet of Lilliano. The imposing structure of the farm dominates the small village; the pieve of S. Cristina is worth visiting and unusual for a pieve in Chianti: a single broad nave. Only the facade remains of the original distinguished by a fine and well preserved limestone facade. The surrounding countryside is well cultivated, mostly vines but also some olive and lower down the valley also wheat. The road down into Castellina Scalo continues down gently and occasional flat stretches tell you are approaching the bottom of the Val d'’Elsa valley. There are lots of farms and estates and at the Cecchi vineyard (after 10 km in all) on the right there is a private road leading to the farm of Villa Cerna. From as early as 1001 the abbey of Isola had property in the area and in 1202 this became part of Florentine territory. There have been so many restorations that it is difficult to make out the original structure but the view is fine from its hilltop position.
The next stage of the route is Castellina Scalo. Here you join the ss 2 and proceed for seven km in the Siena direction. After Monteriggioni, having passed through an area which has been spoiled by stone quarrying, after an uphill but easy slope you take a right fork onto an unmade road signposted Poggiolo. The road rises until you get the latter then it slopes steeply and dangerously down to Badesse, which is of no historical or visual interest. Continue along on a tarmac road following sign for Lornano; the hill is steep and after a kilometre can tire you but it brings you into a hill area.
Proceed towards Castellina; after about 1 km the road is again unmade but does not present any particular problems. There are hills both up and down but fairly gentle ones until you reach a crossroad; turn right here and after a short stretch you join the 222. Here you will come to about 10 km of uphill work and it is wise to engage low gear and take it slowly until you get to Pomona. Initially you run through oak woods but you then come to vines and olive trees. After 4 km at kilometre 50 of the Chiantigiana road there is a left-hand turn off to San Leonino, Topina and Lornano. Continue along the Chiantigiana to Fonterutoli; the hamlet lies on an ancient site but there are few traces of its medieval past. What is certain from the sources is that in 998 privileges were requested from the Emperor Ottone III on behalf of the aretine dioscesis. In the local church of San Miniato on March 29 1201 the famous agreement between Florence and Siena was signed according to which both would leave each other free to conquer Montalcino and Semifonte. In 1208, again in Fonterutoli a peace treaty was signed between the two rival cities; and if one goes from history to legend it is said that it was at Fonterutoli that the border between Florence and Siena was traced because of an encounter between two knights of the respective cities.
On leaving the village the road gets uphill again but not steeply, there are fine views over the valley below and in the distance over to Siena and the area of the "crete senesi". Oak woods and cypresses alternate with cultivated stretches. You encounter a fork for Vagliagli and then another known as Croce Fiorentina. Castellina is now close, the last kilometre first slopes gently downwards and is then on the flat.
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