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The medieval village of Trequanda is crowned by the remnants of the ancient Cacciaconti castle. There is also the parish church of the Saints Peter and Andrea, dating back to the 13th century. It is a beautiful Romanesque-gothic construction with a particular facade covered with white and ochre colour stones forming a geometrical chessboard pattern.

San Giovanni has a castle, which in November hosts the famous White Truffle Market.

The ancient Romanesque church of San Giovanni Battista is close to the castle, while in the lower part of the village lies the most important church in the area San Pietro in Villore.

Within the locality is the picturesque village of Montisi, with its Chiesa dell'Annunziata and its historical grain tower. Here, every year, on the Sunday nearest to the 5th of August (the Festival of the Madonna delle Nevi and a jousting contest - the "Giostra di Simone" - takes place.

Montalcino is completely surrounded by ancient walls and some of the original 19 towers can still be seen, as well as some of the fountains. The impressive fortress, built in the second half of the 16th century is still intact and from its ramparts there are magnificent views across the Val d'Orcia. The surrounding countryside is now devoted to the production of the wine acclaimed throughout the world - the Brunello, and the younger Rosso di Montalcino. Friday is market day

The Abbey of Sant'Antimo, which is about ten minutes from Montalcino is also well worth a visit. You may be lucky and hear the monks chanting.

Torneo di Apertura della Cacce (Tournament for the Opening of the Hunting Season) - Second Sunday in August
This festival marks the beginning of hunting season. The festival starts with trumpeters and drummers. In the afternoon, a costumed procession proceeds to the fortress where archers from the four neighbourhoods (Borghetto, Pianello, Ruga, and Travaglio) compete in an archery tournament.

Sagra del Tordo (Festival of the Thrush) - Last Sunday of October
The festival kicks off with a town crier who walks through the streets announcing the start of the festival to the accompaniment of drums. A dance called the Trescone is performed in the streets. Later a procession to the fortress takes pace with residents in 14th century costumes, rolling flags, trumpets and drums. This marks the beginning of the food fair, which includes typical local dishes such as polenta, pinci, bruschetta etc, as well as Brunello and Roso di Montalcino. At the fortress, the four neighbourhoods (Borghetto, Pianello, Ruga, and Travaglio) compete in an archery tournament and a torchlight procession marks the end of the festivities.