In this paper we report a qualitative study of navigation, wayfinding and place experience within a virtual city. The ‘Cityscape’ is a virtual environment (VE) in part algorithmically generated, and intended to be redolent of the aggregate forms of real cities. In the present study we observed and interviewed participants during and following exploration of a ‘desk-top’ implementation of the Cityscape. A number of emergent themes were identified which are presented and discussed. Observation of interaction with the virtual city suggested a continuous relationship between real and virtual worlds. Participants were seen to attribute real world properties and expectations to the contents of the virtual world. The implications of these themes for the construction of virtual environments modelled on real-world forms are considered.