A live project in Cochrane, Patagonia, termed a journey or travesía, whose aim was to reshape an important threshold between the town and its wilderness setting involved a group of staff and students from PUCV (Pontificia Universidad Católica de Valparaíso) sharing a life in common for a fortnight in November 2013. Taking errantry in post-colonial discourse on identity as its theoretical point of departure, and using the Cochrane project as a case-study, this paper examines an apparent paradox: that in a travesía the creativity of wandering must be allied to a strictly organised plan of campaign. Exploring how and why such a shared journey stimulates not only the acquisition of metis (practical wisdom or artful cunning), but a new capacity to ‘make the land speak’, it draws attention to the risk-taking negotiation skills on which wayfarers depend. Importantly the travesía is shown to be a form of learning-to-build whose arena for insightful play transforms design into an essentially collaborative transaction. Finally, the paper discusses why, as a kind of time-limited ‘trial’ away from Valparaíso to prepare students for the battle of practice, the travesía chooses some but not all the limits and opportunities of ‘liveness’.