In the summer of 2019, members of the CARTography Project set out to re-create the route that Patrick and Joan Leigh Fermor took during their first visit to the Deep Mani in 1951. The project involved meticulously analysing the couple’s notebooks and photographs to glean details about where they had ventured, using least-cost analysis to model their potential routes and ground-truthing the results by walking and boating the routes ourselves. As in much of rural Greece, Mani’s topography has changed substantially in the seven decades since the Leigh Fermors’ journey, with paved roads having replaced many of the Ottoman-era footpaths that locals once relied on for travel and transportation. While the transformed landscape we encountered prevented a complete re-enactment of the Leigh Fermors’ journey, it also offered an opportunity to embody key parts of their travelling experience. The results of our study are twofold: first, a detailed map of the route the Leigh Fermors followed based on our reading of their documentary sources; and second, an assessment of the utility of using least-cost analysis to model the routes of historical travellers.