By all outward appearances, Costa Rica has championed the ethos of conducting tourism on a so-called “sustainable” scale—that is, on terms that aim to bring maximal benefit to people and country while trying to avoid the most egregious offenses common to the industry. The country’s leaders were quick to pledge themselves in policy and in principle to the discourses established by the global community on what would define sustainable conduct, particularly to that which could strike a fine balance between preserving and still utilizing the values inherent in the natural environment. Thus, “green” and “ecotourism” were born as new practices that Costa Rica and many other countries took up in an attempt to still satisfy the contradictory pursuits inherent in appropriative transnational business. Ecotourism mandates an idea of nature as both a resource conserved for the common good while still being enjoyed as a commodity consumed by global tourist networks. Tourism has been well documented as a complicated, contradictory, and nuanced activity for both local and foreign participants. As an industry dominated by the private sector, issues like the consumer’s demands and businesses’ bottom lines must contend with a host country’s receptivity and ability to brand itself as a tourism investment, all while still ameliorating threats of overconsumption and environmental degradation. Thus, sustainable tourism as an idea presents an extremely ambitious goal at best and a complicated if not impossible process at worst. The discourse and implementation of sustainable tourism in Costa Rica proves no different. The case studies of tourism in two Costa Rican coastal towns suggest that its nominal principles and policies continually come up against contradiction, compromise and subversion by the actors expected to normalize them.