In 2006 artist Chemi Rosado Siejo completed construction of El Bowl, a public structure with a dual function of a swimming pool and skate ramp in the La Perla neighborhood of San Juan, Puerto Rico. This article draws upon histories of urbanism and site specific art to examine the history of the structure and its site, located outside the colonial walls of the city. Looking to the development and visibility of the neighborhood since the site’s construction, Jekabson argues that El Bowl is a structure that simultaneously disrupts and supports the growing pervasiveness of media tourism in Puerto Rico.