Caribbean cultural tourism is deeply entwined with American empire and its transoceanic mobilities, yet transnational Caribbean cultural production constantly exceeds and escapes such limiting constructs. In this article, we combine the insights of a cultural sociologist (Sheller) and a musicologist (Martin) to interrogate the meanings of the first Caribbean Festival of the Arts, held in Puerto Rico in 1952, in shaping divergent archipelagic spaces and competing musical itineraries that formed Black Atlantic soundscapes, both imperial and anti-imperial. Following the travels of musical production, dance performance, and cultural tourism marketing around the Caribbean and into North America, we argue that beneath the currents of imperial transnational tourism and cultural consumption there were also countermobilities forming an “alterNative archipelagic” imaginary that connected the Caribbean with Africa and Black America. We trace the ways in which Caribbean music entered North American bodies, with Caribbean musicians bringing surprising trends such as steelpan and Calypso into United States musical performance circuits beyond tourism. The music itself, as well, changed culture and moved people, all over the world, forging other kinds of mobilities and connections contra American imperialism. Music inspired a vision for radical Caribbean and Pan-African unity against the imperial interests of the United States and extractive industries in the region. This tale of an imperial archipelago and its countervailing alterNative archipelagoes suggests that archipelagic formations are open to definition, difficult to stabilize, and always extending outwards beyond the horizon. Constituted by mobilities as much as by islands, archipelagoes are a matrix of transnational cultures capable of remixing, expanding, and resisting imperial power.