Miami is a relatively “new” urban space that has historically been shaped by the Caribbean. By the 1920s, the tentacles of US imperialism ensured that racialized sex tourism in Cuba and the Bahamas—particularly the former—became central to Miami's own success. This essay reveals how Miami's entrenched relationship to the Caribbean provides a necessary transnational view of Prohibition-era culture and politics and the uneasy urban battles that ensued upon the amendment's repeal—two key phenomena in the development of queer cultures and networks. Several transnational tensions nudged Miami toward becoming “wide open,” a status that allowed queers to carve out distinct spaces in the city, particularly during peak tourist season. Much like Miami's “exotic” connections to the Caribbean, queers made the tourist economy work, staffing the service industry and functioning as physical representations of the fantasy and transgression urban boosters marketed, keenly designed as alternatives or supplements to what the Caribbean offered.