This research articulates a relationship between the physical community of Harlem, New York and the digital community comprising TripAdvisor, the world's largest travel related social media website. The purpose of this research is to identify forces of racial commodification in the tourism industry and analyze the role of digital technologies in this process. This research is important because tourism and digital technologies are active sites of racial formation and inequality, and TripAdvisor helps mediate the way they interact. This research employs a mixed-method qualitative approach to articulating the Harlem-TripAdvisor relationship: discourse analysis of online reviews of a prominent cultural tourism company in Harlem, ethnography of that company's tour experiences, and techniques designed to bridge methodological gaps between these two. I find that the Harlem-TripAdvisor relationship produces a three-layered discursive structure, with each successive layer less visible relative to each other. The first—and most visible layer—contains a discourse based in newly emerging conventions of online travel writing. The second layer contains a discourse reflecting touristic valuations of racial difference in capitalistic markets. The third—and least visible layer—contains a discourse reflecting histories and current patterns of racial oppression and inequality. Each of these layers are necessary to create a definition of race emphasizing its supposed benefits to economic growth at the same time it remains a hierarchical and exploitative social construction. / Doctor of Philosophy / This research articulates a relationship between the physical community of Harlem, New York and the digital community comprising TripAdvisor, the world’s largest travel related social media website. The purpose of this research is to identify forces of racial commodification in the tourism industry and analyze the role of digital technologies in this process. This research is important because tourism and digital technologies are active sites of racial formation and inequality, and TripAdvisor helps mediate the way they interact. This research employs a mixed-method qualitative approach to articulating the Harlem-TripAdvisor relationship: discourse analysis of online reviews of a prominent cultural tourism company in Harlem, ethnography of that company’s tour experiences, and techniques designed to bridge methodological gaps between these two. I find that the Harlem-TripAdvisor relationship produces a three-layered discursive structure, with each successive layer less visible relative to each other. The first—and most visible layer— contains a discourse based in newly emerging conventions of online travel writing. The second layer contains a discourse reflecting touristic valuations of racial difference in capitalistic markets. The third—and least visible layer—contains a discourse reflecting histories and current patterns of racial oppression and inequality. Each of these layers are necessary to create a definition of race emphasizing its supposed benefits to economic growth at the same time it remains a hierarchical and exploitative social construction.