My thesis ethnographically examines the changing nature of backpacking for Westerners in Latin America amid a proliferation of mobile computing and social networking. While anthropological and sociocultural research on tourism is extensive, the social scientific literature on backpacking has, thus far, been largely unconcerned with Western Hemisphere countries and the effects of digital technology on this mode of travel. Recent findings suggest, however, that backpacking has currently moved beyond its niche roots as a subculture of independent traveling into a full-fledged tourist industry. My thesis investigates the Latin American backpacking scene to better understand if this is a global trend. The available literature further suggests that today’s backpackers are represented by various subgroups including older and less budget-constrained travelers known as “flashpackers.” Despite using the backpacker infrastructure, flashpackers’ disposable income and relatively expensive equipment places them somewhat beyond traditional backpacker categories. Drawing on ethnographic data collected over two separate multi-sited field sessions in Nicaragua, Honduras, and Colombia, I document the recent experiences of backpackers and flashpackers and evaluate how digital technologies inform and affect their travels.