This paper concentrates on an eminently urban phenomenon, with the accent on urban. The phenomenon in question plays an important role in theories of modern urban culture. City strolling refers to the way we move along while walking through the city. City strolling often is understood exclusively under the hegemony of an optical regime, but this is one-sided. City strolling is related just as much to the bodily experience of the atmosphere of an area in the city. The paper first traces the origins of city strolling. Then it gives a phenomenological description of the phenomenon itself. A rough genealogy of city strolling follows, along with some hints for concepts of urban planning. Then the thesis is developed that city strolling is especially devoted to the exploration of the atmosphere of the city. This leads to a discussion of Michel de Certeau’s “rhetoric of walking” before drawing some conclusions and hinting at a phenomenon closely related to city strolling that has become current in contemporary discussions of urban culture: street art.