Through an analysis of the transformation of Pavones, Costa Rica, from rural village to booming tourist destination, this article examines the interactions between entrepreneurial capitalists and peasant smallholders, and how these relations and roles shifted as a result of sudden economic and social change in the region. It also explores how a nation-state in economic crisis that increasingly relied on the tourist industry responded to conflicts among expats and rural residents. More broadly, this article is about the practice and politics of development in the contemporary rural Global South. It traces the archival trail of Daniel Fowlie, a US surfer, developer, and business executive who played a central role in the transformation of Pavones into a famed international surfing destination and who, in the process, was imprisoned for international drug trafficking. Building on scholarship about travel and exploration literature, the article examines Fowlie's discursive representation of Pavones and Costa Ricans and connects it to larger, dominant discourses in surf and travel media about narratives of discovery and development that often embody an imperialist nostalgia to inculcate a particular idea about time and industriousness as part of development.