The visual, aesthetic and symbolic effects of height on the urban environment shape the perception of tall buildings by residents and visitors. The proliferation of tall buildings in the, until recently, low skylines of Nicosia and Limassol in Cyprus has transformed how people view the two cities’ current identities and how they foresee their future directions. In order to understand how tall buildings affect the Cypriot urban environment, this paper investigates their visual presence in Nicosia and Limassol, tracing their relationship with the landscape, the townscape, and the social texture of the two cities, to assess their role as potential place making—or place breaking—agents. Methodologically, our study looks successively at three levels of associations: the land, the city and people, to understand the visual and symbolic readings connected to the emergence of tall buildings. It begins by locating the position of tall buildings in the cities’ skylines and their relation to other landscape elements, examining the difference between the clustered arrangement of Nicosia and the linear arrangement of Limassol. It continues with regarding tall buildings from the pedestrian level, to understand their function as wayfinding elements and urban landmarks. Lastly, it presents the results of an online survey, to discuss people’s views on the effects of tall building development in the identities of the two cities. Our study indicates that the two cities’ skylines appear fragmented, tall buildings are not widely regarded as wayfinding elements, while the lack of accessibility disconnects them from the public. While individual tall buildings are promoted as sites of luxury, and symbols of a hopeful future for both Nicosia and Limassol, images of the two cities’ skylines have yet to be constructed, both literally and in collective narratives, as part of their urban identities.