The paper focuses on a remarkable painting of the ‘Holy Family and Saint Francis of Assisi’ preserved ab antiquo in the church of Santa Maria della Misericordia in Massa Lubrense and traditionally attributed to Guido Reni. On the basis of new documents, in addition to attributing the painting to Massimo Stanzione, the essay also clarifies the reasons for and significance of this presence in a secluded hamlet on the Sorrento coast, associated with the figure and family origins of Vincenzo Cioffo, an important person in Naples in the middle of the 17th century who grew up in the circle of the Orsini family. Archival research has also brought to light other episodes in Cioffo’s patronage, enabling in particular the recovery of an altarpiece by Luca Giordano with ‘Saint Vincent Ferrer’, destined for the Neapolitan church of Gesù e Maria and hitherto unknown to scholars.