We report a qualitative study of navigation, wayfinding, and place experience within a virtual city. “Cityscape” is a virtual environment (VE), partially 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 desktop implementation of Cityscape. A number of emergent themes were identified and are presented and discussed. Observing the 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 modeled on real-world forms are considered.