Castelfiorentino is situated in the administrative district of Empoli-Valdelsa, between the Arno River Valley and the northern side of Elsa Valley.

In the Middle Ages this area surrounded two extremely important ways, Via Francigena and Via Volterrana, which were transition points for pilgrims and wayfarers coming from the North of Europe to Rome.

The village of Castelfiorentino was built near the crossroads, over an ancient Roman settlement, called Timignano. It was Feud of Cadolingi and later belonged to Counts Alberti: in the XII century, Castelfiorentino was preempted by the bishop of Florence and underwent the conflicts between Church and Emperor and between Siena and Florence, of which it used to be a very important outpost. For that reason it became official seat of the Podestà, obtained the priviledge of the red lily on its flag and the name turned into Castelfiorentino in 1149.

In 1260, after the battle of  Monteaperti, Castelfiorentino became famous because the peace between Siena and Florence was signed there. Since the XII century, this lovely town has had a great political, economical and artistic importance, due to its special position in between Florence, Pisa and Siena: three fundamental  towns for the Italian Renaissance. This significant mixture of art, history and tradition has largely influenced the local trends and life-style, creating a unique cultural and artistic patrimony .

There's a huge range of events and happenings in Castelfiorentino all over the year. Among the main local festivals, “In canti & banchi”, during the fourth week of May, is certainly the buttonhole. In canti & banchi is a street theatre and ballad singers festival, that fills up the old town centre's streets in a magic atmosphere. You will be able to attend suggestive exhibitions of art as well as antique trade and collecting markets.

The celebration of St Verdiana (on the 1st of February and the Monday after Whitsunday) the patron saint of Castelfiorentino is a special happening that you cannot miss: along with the procession, you will find numerous stands with various and picturesque merchandise.

Some other relevant folkloric festivals are the “Spring” and “Autumn” ones, wit live music concerts, unmissable theatrical appointment and food and wine festivals. 
If you are keen on Italian literature, the big event, scheduled in February, is the "Premio letterario": an “open” competition, with unpublished poetical and fiction works about themes that change year by year. There's also a special prize destined to a contemporary famous Italian author.

To summarize... the main appointments are:

  • "Festa di St Verdiana":  1st of February and the Monday after Whitsunday
  • Spring Festival: the third Sunday of March
  • Autumn Festival: the third Sunday of October
  • Winter Festival: the second Sunday of December
  • "In Canti & Banchi": the fourth week-end of May
  • "Castello a Tavola", to taste local wine-and-food products: the third sunday of June
  • Popular Theatre festival: the last week of June in Castelnuovo d'Elsa
  • "Festa della Rificolona": 7th September
  • Il giorno piu' dolce dell'anno – The sweetest day of the year : the third Sunday of September in Castelnuovo d'Elsa
  • Choral singing show: second Sunday of November.

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