In the Middle Ages the importance of the Val d'Orcia was tied mainly to the 'Francigena', principal European Road, that crossed the valley longitudinally for all its length.

In this road there were numerous 'Spedali' (Hospitals) between which the castle of Spedaletto, a grandiose strengthened complex built in the 12th century that, since 1236, was managed by the Spedale of S.Maria della Scala in Siena and it was called 'Spedale of the bridge on the river Orcia'.

The Spedale also entertained important wayfarers such as Charles II d'Angio and Pope Pio II Piccolomini. The castle has a square plan with towers at every angle, machicoulis with beautiful brackets in stone and battlements along the entire perimeter, a splendid strengthened gate with a mighty keep at its defense. Enetring the outer ward we find on the left of the gate the church of the Spedale with a splendid façade enriched by a rose window and a portal with Gothic arch, on the right the gate to the inner ward, adorned with coats of arms in stone.