The early activity in Perugia of Domenico Alfani intersects with that of the young Raphael, who appeared in the city in 1503. Testifying to their friendship is the autograph sheet by Sanzio in the Wicar collection of the Palais des Beaux Arts in Lille, addressed to the young «menecho». Proposed here is a new interpretation of the text on the sheet, and the identification of a Perugia correspondent of Raphael that has never before appeared in the critical literature. In a passage of his annotation Raphael writes: «Recordo a voi menecho che me mandiate le istramboti de riciardo di quella tenpesta che ebbe indando i uno viagio». Scholars have always identified the «riciardo» he mentions as Ricciardetto, a character from canto XX of Luigi Pulci’s Morgante, but now the personage in question is identified as Riccardo Bartolini (Perugia, late 15th c. – Perugia (?) 1529), a well–known intellectual and literato then active in Perugia, who was a prominent figure in the city’s politics and culture as well as a professor at the Umbrian university. Bartolini’s literary production, mindful of Homeric and Virgilian models, boasts a number of texts that enjoyed fair success, among them the Odeoporicon, published in Vienna in 1515, and the Austriados libri of 1516. The phrase «istramboti de riciardo» is here connected to the descriptions of storms and shipwrecks Bartolini uses in the Odoeporicon to comment on his perilous diplomatic journey to northern Europe in the entourage of his uncle Mariano Bartolini, a professor of civil law, diplomat for the Baglioni, and uditore di Rota under Julius II. In addition, the «predicha» that Raphael has the goldsmith Cesare del Roscetto request, is here identified with the Predica d’Amore by Marco Rosiglia — a still little known figure then active in Foligno and familiar with the court of Urbino — a text that Raphael could well have known. The autograph drawing by Raphael visible on the recto of the sheet is crucial for a study of the gestation of the Holy Family with Saints Anne, Joachim and Young John the Baptist completed by Alfani for the Carmelite church in Perugia, a work that must be dated 1510–1511. It is moreover demonstrated that the altarpiece was uniformly carried out by Domenico Alfani, without the help of a certain Anselmo who scholars have always speculated was the co–author, and who in point of fact, does not exist. The chronological reordering of Alfani’s early works allows us to rule out that he was the painter of the cimasa of the Pala Baglioni.