New Orleans and Havana, once nodes on the same circum-Caribbean circuit for trade and travel, both profit from their musical reputations in economies that are greatly dependent on tourism. Political and economic changes have altered previous versions of relationships between the two, creating in the twentieth century a kind of disjuncture – a temporal and imagined gap – that alters understandings and experiences of their spatial proximity. At the same time, their intertwined regional histories and contemporary culture are mobilized in parallel contexts of economic need and global tourism markets, suggesting that they may have concerns, challenges, goals, and aspirations in common. As two cities with strong musical voices that circulate widely beyond their geographical, physical locations, they are both prominent and productive examples through which to examine the musical-touristic encounter across national borders but within the same region: the circum-Caribbean . Many iterations of musical self-image of both New Orleans and Havana contain at least a trace of the other (Moore 1997; Sublette 2004; Sublette 2008; Dawdy 2008). Engaging with a narrative of American exceptionalism rooted in New Orleans that acknowledges the Caribbean in Jelly Roll Morton’s “Spanish Tinge,” I follow that narrative to Cuba, sketching a constellation of connections and relations that suggest not only musical “influence” located in the misty past, but a shadow-narrative (or palimpsest, or blueprint) of connections that are – in addition to being historical – contemporary, cosmopolitan, and lived and embodied in the present. In locating connections in the present, I argue that it is possible to foster ethical and mutual recognition and collaboration that may better serve tourists and locals in both cities(and beyond); agents in the exchange – tourists, “travelees” (Pratt 1992), governments, private businesses – have opportunities to forge connections that are meaningful now, for example finding solutions to the management of heritage tourism that ceases to leave out “culture-bearers” as beneficiaries. This dissertation takes as its focus the musically-mediated touristic encounter in Havana and New Orleans. It investigates the dynamics of tourism and musical expression and consumption, using an orienting framework of “the archipelago” to draw out the multidimensional, multidirectional, and multivalent possibilities of relations. In this approach, I attempt to de-isolate New Orleans and Havana from each other, contributing to a broader body of scholarship that moves towards a relational understanding of music and its functions in the circum-Caribbean. In the media, literature, historical documents, and ethnography that inform this dissertation, I perceive a kind of re-emergent archipelago of a sonic “repeating island” (Benitez-Rojo 1992), constructed through touristic encounters, often characterized by utopian desires.