This paper will provide an overview of the fundamental changes that the cruise ship business has undergone with the emergence of capitalist globalization and in the context of the Caribbean region. Rising profits and investments in tourism during the later decades of the 20th century and into the 21st century have been an important part of the globalizing economy. This has been a consequence of both the major technological and organizational developments of global capitalism, but also, and most importantly, of the global system’s changing social and class relations. The shifting social relations and productive activities that undergird the cruise ship business have meant gains for some involved, most especially, transnational capitalists, and exploitative and contradictory dynamics for many others. Annually millions of tourists from high consuming sectors worldwide partake in brief holiday escapes aboard cruise ship vessels. At the same time, the cruise ship business has become an oligopoly, controlled by a handful of large companies, that has driven many competitors out of business or acquiried them. Labor in the business has become more flexibilized, with low-wage workers (from a variety of nationalities) whose activities are increasingly standardized, monitored and micro-managed. While moving away from indicative development planning (with an eye to national goals), state policymakers in the Caribbean, for their own social reproduction, increasingly promote the interests of transnational capital such as with the cruise ship business. Importantly, labor and environmental protections have been stymied as the cruise ship companies, adept at public relations and skirting regulations, remain largely unaccountable.