The town of Guardistallo, with a population of 1000 inhabitants, is set between Maremma and Northern Tuscany in the province of Pisa and it rises at 278 m. a.s.l. Its homonym medieval castle, the church of the Saints Lorenzo and Agata and Villa Elena can be admired here.

The settlement of the area probably dates to the Neolithic (more than 2000 years before Christ) as it is shown by stone and metal objects found in the territory and kept in the archaeological museum of Florence. Later, also the Etruscans inhabited this area but there are no evidences of the Roman times. Instead, the Lombards certainly settled here and they gave this town its name from the words "wardan" (guard) and "stall" (place).
Around the VII century A.D. this population came to Italy in the wake of the Barbarian invasions and built a small castle where the town rises today.
Around the year 1000 the castle belonged to the Counts Della Gherardesca who gave it to the bishopric of Volterra in 1154. In the XIV century, the village was subjected to the domination of Pisa and tried to avoid it in 1345. Once the rebellion failed, the town remained under the aegis of Pisa until the beginning of the XV century, when it anticipated the destiny of the sea-faring republic being subjected to Florence.
In 1406, by the time Guardistallo had sworn its loyalty to the Grand Duchy, the town was a city-state, already. The troops of the king of Naples, Alfonso d'Aragona, occupied it in 1447 and destroyed most of its defensive structure, exception made for the count's ancient castle.
No information about Guardistallo was available until 1739, when it was transformed into a feud and given to the Florentine Marquis Carlo Ginori together with other territories of Pisa. A chronicler of the time described it as a decaying place with its fortress deteriorating , water shortages and a growth of woods that was jeopardizing the town. With the agrarian reform wanted by the Lorraine in 1776, a new class of landowners strengthened the territory and enhanced its agricultural production.
The terrible earthquake that hit Tuscany in 1846 further compromised the quality of the town's urban planning. The church, the bell tower and the cemetery were destroyed by the violence of the earthquake. The current layout of the village is the one created during the huge reconstruction works carried out later.
In the second half of the XIX century, the church of the saints Lorenzo and Agata, Villa Elena, where the Marchionneschi family went to live, and the theatre were built. Soon, Guardistallo became the "small Paris", a resort place for many famous and wealthy Tuscan families.
During the Second World War at the acme of the Nazi occupation, one of the cruellest episodes of the fight between partisans and Germans, who were going to be defeated, took place. On 29 June 1944, the Nazi-Fascist troops took a violent reprisal before their withdrawal and shoot 63 defenceless civilians not far from the chief town. In these circumstances, the figure of Father Mazzetto Rafanelli was emblematic, because he avoided another slaughter by giving himself to Germans in exchange for the liberation of 120 people.