Abstract Between the late nineteenth and mid-twentieth century, the ongoing crises of the late-colonial Caribbean mingled with an emerging trend: white American and European tourists who flocked in growing numbers to the tropics in search of pleasure, leisure, and adventure. As these travelers arrived in port in the era before commercial flight, they encountered a ubiquitous scene: boys and young men in small rowboats, who would surround the incoming steamship and, nude or nearly nude, dive in the tropical surf for coins tossed overboard. Images and accounts of these coin divers circulated widely in travel media, and were instrumental in constructing a tourist-friendly vision of the Caribbean seaside as exotic, picturesque, erotic, and accessible. In colonial Caribbean sources, however, coin divers were viewed not as an alluring spectacle but as a criminal threat, somewhere between beggar, truant, and sex worker. The divers themselves were working-class youth inhabiting a harbor-world on the periphery of a stratified and shifting society. They experienced firsthand the transition from Caribbean colonialism to mass tourism, and used the harbor to enact a limited autonomy and demand recognition within a system that provided few meaningful alternatives. Analyzing the tensions between these contrasting modes of power—one that commodified and one that criminalized—we can better understand the complex dynamics in the transition from plantation colonialism to tourist neocolonialism in the Caribbean.