Castelnuovo Berardenga represents the border between Chianti and the territory of Berardenga.
The village is placed between two very different territories: Chianti, with its soft and fertile bends on one side, and the harsh and dry territory once possessed by Bernardo Berardenga, on the other side, with olive trees here and there. This is the reason why Castelnuovo is one the few villages which hosts a Landscape museum.
Situated in the high valley of the Ombrone where the landscape of the Crete Senesi already begins to be delineated, Castelnuovo Berardenga is the southhernmost Commune in Chianti. Originally, it was at the centre of the Ugurgeri della Berardenga gamily, to which it owes its name. But its origin as a castle was decreed on 26 July 1366 by the Great Council of the Senese Republic, in order to defend the zone from the incursions of bands of mercenaries. The work, directed by Mino Dei of Siena, were finished barely in time.
Even before the workmen had applied the finishing touches to the walls that surrounded the upper part of the hill, Castle Berardenga-called "new" to distinguish it from the more ancient fortifications of the zone, such as Arceno or Valcortese-was in fact assaulted by the militias of the condottiere Giovanni Acuto, who was in the pay of the Florentines.
The siege, which ended in 1382 with the surrender of the fortress and its sacking, did not, however, prevent the castle's returning to the hands of the Sienese, who subsequently were to defend it courageously in 1478 and 1479 from the ambushes of their eternal rivals.
It was only in 1481 that the Sienese decided to complete the fortifications and establish a garrison there. A few yaers later, in 1489, the betrayal of Count Francesco Landi caused the fortress of Castelnuovo to fall into the hands of Florence, but after a year's siege it returned to the hands of the Sienese. Later on, in 1511, with new and powerful fortifications, Castelnuovo was ceded by the Republic of Siena to Belisario Bulgarini, who was podesta of it for many years. It subsequently passed under the dominatio of the Bellannati family, who kept it until 1526.
The following year, the castle returned to the Sienese, and witnessed the passage of Charles de Bourbon with his troops; in 1538, it was also visited by Pope Paul III on his way to Nice.
When Siena ultimately fell, it became part of the Grand Duchy of Tuscany.
The urbanistic element that predominates today is unquestionably the majestic Villa Chigi Saracini, with a magnificient park that can be visited on holidays and week-ends, encircled by a surrounding wall on which two spectacular doorways open.
A walk through the historic centre, which in its development and several habitations recalls the 14th-century scheme, is definitely worthwhile, as is a visit to the main church where two interesting paintings are preserved: a Madonna by Giovanni di Paolo (1426) and another wooden panel depicting the same subject, by Andrea di Nicolò.
The village of Castelnuovo is also part of the Chianti Cycling Park, and bike certainly represents a good mean of transport for an alternative and charming visit of the territory. There are numerous villages that are worth a visit: Montaperti for instance was the place where a battle took place, mentioned by Dante in the Divine Comedy (Hell, 32nd canticle). A pyramid was raised up in memory of the battle. The Certosa of Pontignano was founded in 1343, and reconstructed during the first half of the 16th century.
Abbadia Monastero has maintained its original name, but today the religious buildings have all been replaced by a villa and a farm house.
Montalto, instead, is still a manor house provided with towers. Last but not least, the small village of Picina, with its medieval parish, is also worth a visit.