Automobiles significantly changed access to leisure for Americans at the beginning of the twentieth century, spawning interest in and growth of resort towns like Miami, Florida. The occupation of chauffeur was a frequent site of both class conflict and anti-Black terror. Yet the car operated as a liminal site of subjectivity in which Black chauffeurs determined some parameters of their experience of both work and pleasure. Black chauffeurs in Miami in the 1910s were at the vanguard of efforts by local Black communities to create and claim pleasurable space and its attendant leisure via driving in a profoundly racist and exceptionally dangerous touristic climate. At stake was access to a commodity and a profession with an exhilarating potential to upend social, political and economic norms, remolding communities in ways that promised leisure for local Black motorists, chauffeurs, and vacationers. Black automotivity in Miami disrupted aspects of the city’s system of racial capitalism and established the car as a potent site of refusal, work, and pleasure.