Digital-free tourism (DFT) describes tourism spaces where internet and mobile signals are either absent or digital technology usage is controlled. By employing critical discourse analysis of over 450 media texts produced between 2009 and 2017, the study reported the conceptual understanding of DFT, the ways the media representation has changed over time and explored the broad social context and debates in which the concept is embedded. By reading and reviewing the texts, unsupervised (automatic) Leximancer analysis, and manual coding, a shift in the representation of the concept was established. Initially framed simply as a reaction to the pressures of abundant connectivity in the years 2009–2015, recently the possibility for human flourishing, well-being and an enhanced lifestyle have emerged. Holiday making in a digital-free environment is intimately linked to the ways individuals can manage their contemporary relationships and experiences rather than be controlled by the technologies others have created.