At the entrance to the avenue leading up to Palazzo Massaini, in the countryside north-east of Pienza, stands the small chapel of San Regolo. The "palazzo" is in fact a well-preserved fifteenth-century castle, in all likelihood once owned by the Cacciaconti, lords of Montisi; the chapel, plain and tiny, marked its access from the road.
For centuries the building housed a statue of Saint Regulus attributed to Domenico di Niccolò dei Cori and datable to 1430-1440. The sculpture is no longer here: it is now on display in the Diocesan Museum of Pienza.
What to see
Take the chapel for what it is: a small country oratory whose interest lies in the ensemble it forms with the entrance avenue and the well-preserved castle behind it, a reminder of the families who once controlled these lands between Pienza and the Val d'Asso.
The sculptor whose work was venerated here deserves a note: Domenico di Niccolò (c. 1363-1453) was among the most sought-after carvers in early fifteenth-century Siena, and his nickname "dei Cori" — "of the choirs" — came precisely from his skill in woodcarving, sealed by the choir stalls of the chapel in Siena's Palazzo Pubblico.
Visiting
The chapel is seen from the outside, at the start of the castle avenue, along the country roads that cross the farmland north-east of Pienza. It is a quick stop, best folded into a drive or bike ride between Pienza and the villages of the Val d'Asso rather than a destination in itself.
Our editors' tip
Finish the story in town: the fifteenth-century statue of Saint Regulus awaits you in the Diocesan Museum of Pienza, on corso il Rossellino. Seeing the chapel in its farmland setting first and then the sculpture in the museum rooms shows how many works from Sienese country churches have ended up behind glass — and it gives the little statue its history back: not a collector's piece, but the image before which the farmhands of a fortified estate once stopped to pray.