Over the past 5 years the [Team] team at the University of [Institution] has been experimenting with new ways of teaching the studio practice outdoor with direct learning from the interaction with the build environment and people in the urban context. Preliminary findings have been published in Authors (2018). This paper presents new findings with the case study of New York, where students have been mapping the impact of digital technologies on the use of physical space. Students have been using a series of tracking apps to gather on-site data that have been interpolated with drawing-based models elaborated in class. The first part of the paper outlines the theoretical framework that underpins these activities, including a brief discussion on key case studies (Lupton 2016). The second part describes the studio activities, highlighting the findings, with the support of a set of maps and digital visualisations. The third part discusses the findings offering a generalisation of the results of this study within the wider context of architectural education. This contribution addresses the conference’s themes by reflecting on the importance of on-site mapping, and observational and representational activities with a critical evaluation of the depiction of urban life in the renaissance through life sketching (cf. Zimmerman and Weissman 1989) and their possible connections with today’s digital technologies (Carpo 2013) in architectural education. Secondly, everyday routines of urban life are reconsidered as main elements for students to design future cities. In particular, social accounts (Gehl 2004) are included in this study, and the importance of future architects to be well-versed in a variety of disciplinary fields (technological, social, cultural and political). Finally, this paper offers a speculation into future models of learning by looking at how technology offers new venues for students to observe, analyse and understand cities and the people living in it.Peer reviewe