Despite being a generation apart and thus unlikely to have ever met, both Artemisia Gentileschi (1593–c. 1654) and Barbara Strozzi (1619–1677), frequented, and were celebrated by, a close-knit network of Venetian poets, librettists, musicians, artists, collectors, and patrons closely linked to the infamous Accademia degli Incogniti. The Incogniti valued wit, improvisation, performance, and ribald humor, and were particularly fascinated with in the so-called “questione della donna,” which examined, often irreverently, the status of women in ancient and modern society. This chapter explores what can be gleaned about the interactions between artists, musicians, collectors and painters in little-studied years that Gentileschi spent in Venice (1626-1629?), such as the lawyer, letterato, and collector and Giacomo Pighetti, the writer Giovan Francesco Loredan, and the painter Alessandro Varorari, known as Il Padovanino. These connections, I propose, help elucidate the works Artemisia painted in these years, even if many of them are lost or unidentified.