Cultural constructions of gender and age may be challenged within politically and socially progressive leisure environments, like Key West, that promote social deviance and out-group acceptance. However, this possibility receives limited scholarly attention. Addressing this gap, our study applies a framework that highlights gender and age as performances and uses interviews ( n = 77) collected in 2017 and 2018 at Key West’s Fantasy Fest, an annual carnivalesque event characterized by body displays of nudity, body paint, and costume. In this first systematic study of Fantasy Fest, data analysis revealed four themes centering on gender, age, and bodies—displaying diverse bodies; judging bodies; limiting body displays; and reinterpreting body-related norms. Key West’s cultural ideology of inclusion allowed both young and old participants to perform gender and age in ways that contributed to a more liberating environment celebrating a range of bodies—though performances were constrained by inequalities. Bodies, especially women’s, were subjected to judgments of their sexual appeal that led some, especially older women, to limit their displays. Our findings, nevertheless, suggest progressive, carnivalesque leisure environments’ potential, however fleeting or bounded, to disrupt everyday performances and broaden conceptions of gendered and aging bodies by reinterpreting the norms surrounding them.