As opposed to traditional nomads, backpackers, or tourists, digital nomads are defined as Internet-enabled remote workers, who maintain a focus on connectivity and productivity even in leisure. This essay discusses the relationship between Instagram and the digital nomad from a theoretical perspective, proposing a critique of the aesthetics and urban politics that underlie this figure. Inspired by recent theories that combine geopolitical and technological insight with a speculative approach, the article positions the digital nomad as a cultural avatar of contemporary neoliberalism, which celebrates a depoliticized aesthetics of work and helps establish a material geography of globalization through social media. In particular, the essay leverages the concept of tagging (not only intended as the use of hashtags like #digitalnomad, #solotraveller, or #remotework, but also geotagging) as a tool for cultural critique, discussing Instagram as a key site of intersection between the imaginary appeal of the traveling entrepreneur and the material effects of globalized gentrification. The conclusion provocatively suggests that, with the increasing economic and geopolitical influence of digital nomadism, Instagram might become a site of negotiation of the figure’s culture and aesthetics, potentially steering them toward a more radical re-imagination of borders and life beyond work. By offering a cultural critique of the digital nomad, the essay contributes to critical discourse on Instagram as a cultural platform.