The Bassetto property was established during the 12th Century on the New Francigena, one of the alternate paths of the medieval pilgrimage route between Canterbury and Rome. While the main route, the Via Francigena, passed over the hills near San Gimignano, the New Francigena, ran through the valley parallel to the river Elsa, connecting Castelfiorentino, Certaldo, Vico D'Elsa, Poggibonsi and continuing onto Siena.
Bassetto began as a Benedictine monastery commissioned by the Counts Alberti of Certaldo Alto in 1164, by concession of the Emperor Federico Barbarossa. It operated as a monastery until 1415 when the town became the seat of the Florentine Vicariate. The land in the valley along the River Elsa was originally swamp land, and the surrounding hills rocky and unsuitable for agriculture. Led by the Benedictine monks, using their expert knowledge of agriculture, Bassetto became a thriving agricultural community.
'800
In the second half of the 18th Century, the Italian State dispossessed the church of all its properties, including Bassetto, offering them for sale on the open market. Under the threat of excommunication by the church authority for those who purchased former church lands, the properties remained unsold. However in 1859 Piero Guicciardini, an eccentric intellectual who was exiled to Great Britain in 1851 for founding the Evangelical Church in Italy, returned to Florence and, with obvious disregard to the Church's threat, purchased Bassetto and another farm in Vico D'Elsa.
Upon his death in 1888, the property was inherited by Piero's nephew, Francesco Guicciardini. Francesco was an outstanding member of the family who, under the governments of Sonnino and Starabba, became the Minister of Agriculture and then the Minister of Foreign affairs. Under Francesco's guidance, the Fattoria del Bassetto achieved its highest productivity as a farm. Comprised of 30 different plots, with a total area of 280 hectares, the farm produced tobacco, corn, wheat, olive oil and silk worms. In 1890, Francesco expanded the existing compound by building a large cellar, partly excavated under the hill behind the main building, containing two parallel vaults 60 meters in length.
'900
Upon his death in 1915, the property passed to one of his daughters Dianora, who in 1912 had married the Duke Giuseppe Canevaro di Zoagli, and so the property passed into the Canevaro family. Since this time, Fattoria del Bassetto has remained in the Canevaro family and is currently owned by their granddaughter Dafne.
Up until the end of the Second World War, agriculture was the primary basis of the economy in the region. At this point, due to the advent of industralization and urbanization, the share farming system of the region, which had sustained the farms and local economy, began to decline. Over a period of about ten years, farm workers moved from the country to nearby towns for more lucrative employment, resulting in the decline of the agricultural economy of the region. Without labour to help run and maintain the Fattoria (farms) the farm owners found themselves in times of economic hardship. Cottages and houses abandoned by the departing workers began to deteriorate. In order to avoid a similar fate, the Fattoria Bassetto and other farms and businesses in the area moved away from agriculture and, taking advantage of the region's natural beauty, culture, food and wine, turned Certaldo and the surrounding areas into the tourist and recreational attraction it is today.
