Carnival, Royal Caribbean, and Norwegian—the most profitable cruise lines today—emerged between the late 1960s and early 1970s, as the elitist leisure ocean travel industry attempted to recover from economic downturn. These mass-market lines targeted an American middle class that increasingly had the desire and financial means to travel. They secured much of this untapped market by creating packaged vacations that responded to the needs and tastes of a middle-class clientele. Drawing on cruise advertisements, newspaper articles, ephemera, industry documents, travel writing, and memorabilia books, this dissertation analyzes how these three companies used cultural and geographic referents to produce cruise vacations, responding to an increased consumer interest in cultural sampling as an accruement of economic globalization. Findings suggest that cruise ships offered their owners a space to arrange simulated interactions with global cultures—a practice that soon extended to Caribbean cruise ports as these companies gained the market power to influence encounters there. This complex collision of global cultures was advanced by a goal to offer passengers opportunities to discover new worlds. However, many of the cultural representations displayed on cruise ships were pastiches—essentializations drawn from popular media forms and based in Eurocentrism. These were meant to be entertaining, not accurate, representations. Nevertheless, as themed environments gained momentum, these cultural forms helped to transform ships into destinations in their own right—a process through which cruise lines produced a captive audience to siphon passenger spending from the Caribbean. At the same time, cruise lines leveraged their mediating power and economic influence to hide from passengers the supposed poverty, crime, and disease at Caribbean ports, and even the mundanities of daily life there, while increasingly installing mechanisms to appropriate spending from those who chose to debark the ship. These processes intensified as the decades advanced. This study thus finds that cultural homogenization did not result in an immediately apparent reduction of difference, because difference was profitable and central to the mass-market cruise industry’s advertising strategies. However, the surface-level cultural heterogeneity that cruises offered was reduced through a homogenizing vision that balanced novelty with passenger comfort, engagement, and convenience in support of corporate profits. The resulting cultural production process was not suggestive of glocalization, but rather a new phenomenon meriting further research.