The contemporary cruise ship industry is one of the most visible and global economic activities. It is also one of the fastest growing segments of the tourism industry, which is often considered to be the world's largest. This research explores the most fundamental element that makes this growth possible: human labor. With this dissertation, I focus on Filipino seafarers working aboard cruise ships in order to illustrate how this most globalized industry is organized around a particular geography of work in the global economy that creates a skilled yet disadvantaged labor force. I argue that particular groups of people are selected to work in the global economy through a complex system that marks workers with desirable traits. These discourses frame how cruise lines, labor recruiters, and even workers themselves view Filipinos, thus serving to naturalize their position as the "perfect" seafarer. These discourses are all the more powerful considering that cruise lines are striving to find not only those workers with the right qualities, but also those that are the most flexible. Cruise lines, however, have found that geography sets limits in this regard, and those that are the most flexible are not necessarily well suited to work aboard luxury vessels. Finally, this research also highlights the risks that Filipino seafarers necessarily embody in their working lives on ships. Recent legal decisions in U.S. courts relating to the employment and protection of international cruise ship workers have repositioned the historical relationships between seafarers and their employers, and have created a new extraterritorial legal space in which seafarers' rights are diminished. In this context, Filipino seafarers find themselves embedded in a dynamic transnational system which facilitates their entry into the cruise industry, yet structures a diminution of their protection under law. In summary, this dissertation illustrates that the contemporary form of leisure represented by the cruise industry is entirely reliant on inequalities within the global system. In short, cruise vacations could not exist in their present form without a highly uneven world.