While urban boosters crafted Miami’s fairyland for a white and moneyed clientele, the city’s working-class, transient gender and sexual renegades similarly asserted their own spaces in the developing landscape. This chapter uncovers how queers, primarily those listed in the historical record as men, traversed Miami’s public and semipublic spaces. It focuses on the ways mostly working-class, transient men transgressed gender and sexual norms in Miami. In addition to noting how the city’s queer archetypes challenged the very categories that differentiated “women” from “men,” this chapter also notes some of the institutions that surveilled, regulated, and criminalized the bodies of women whose sexual appetites were read as “unnatural.” In tracing arrest, medical, and commitment records, along with other contemporary sources—such as newspapers, state and local laws, and judicial testimonies and hearings—this chapter reconstructs the urban presence of gender and sexual transgression outside the theatrical stage. It demonstrates how state and local laws criminalized gender transgression and homosexual acts, as well as the uneven prosecution of such activities based on judicial interpretations of class, race, ethnicity, age, and (dis)ability.