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Although leisure is a gendered realm, less is known about how women and men experience leisure within socially-tolerant environments. Described by Anderson (2011) as “cosmopolitan canopies,” these pluralistic spaces can promote civility and camaraderie among diverse peoples – which could conceivably aid in diminishing gender inequities in leisure. While cosmopolitan canopies are socially-tolerant and pluralistic in nature (i.e., socially, racially, and ethnically diverse), some canopies also become defined by their tendency towards social and political progressiveness. In their quest to purposefully enact social change, “progressive cosmopolitan canopies” may in fact be even more instrumental in the reduction of inequalities in leisure – particularly those progressive canopies that concentrate on leisure. The canopies that form within progressive leisure environments may shift gender ideologies and grant women, and other subordinated groups (e.g., sexual and other minorities), more power within their leisure experiences. Through ethnographic fieldwork, this research analyzes how Key West, Florida, a progressive leisure-based cosmopolitan canopy – defined by its forward-thinking socio-political and cultural ideologies – intersects with gender inequalities (and other social statuses) to affect leisure experiences. The data presented two processes through which gender inequalities were combatted in leisure experiences– creating progressive narratives and doing deviance. This fieldwork expands our understanding of leisure as a gendered realm by examining social interactions within shared leisure spaces – while concurrently elaborating upon our knowledge of cosmopolitan canopies.