Zingari were an unwelcome minority controlled through draconian legislation, but fictional gypsies made regular appearance in comic theatre and strophic song. Gentlemen could assume the mask of the gypsy during carnival and entertain various fantasies of transgression—cross-dressed in terms of gender and status, young men could proposition ladies and attempt to cross the boundaries of their homes. For most of the sixteenth-century, gypsy women seem to have been played by men; Vittoria Piisimi’s performance at the 1589 Florentine wedding celebrations is one of the first references to women putting on this mask. Piisimi seems to have started a trend, for Francesca Caccini composed a Ballo delle zingare (1615) for another wedding. (Gypsies’ reputation for fortune telling made them useful characters in dynastic celebrations.) This paper explores Florentine gypsy fictions with particular attention to an apparent distinction between a ‘masculine’ Carnival tradition and a ‘feminine’ theatrical court tradition.