Mobility has long been a central concern in research within the Computer-Supported Cooperative Work (CSCW) community, particularly when it comes to work and how being on the move calls for reorganizing work practices. We expand this line of work with a focus on nomadic leisure practices. Based on interviews with eleven participants, we present a study that illuminates how digital technologies are used to shape and structure long-distance cycling. Our main analysis centers on bike touring as a nomadic leisure practice and on how it offers a radical departure from traditional modes of structuring work and life, and thus, complicates the relationship between work and leisure. We complement this with an account of managing the uncertainties of nomadicity by focusing on participants’ experiences with arranging overnighting and network hospitality. We offer this study, firstly, as one response to the call for more diversity in the empirical cases drawn upon in theorizing nomadic work and leisure practices, but more productively, as an opportunity to reflect upon the temporal and spatial logics of digital technologies and platforms and how they frame our attitudes towards the interplay between work and leisure.