Abstract: This article examines the problem of symbolic urban space, as well as reveals the essence of a city as cultural text, while the signs and symbols as the information carriers. In the course of this research, the author analyzes the structure and principles of the establishment of architectural space, which is a complex multilevel system, integrated symbolic formation, which remains in constant pursuit of the own architectural image. The study of architectural space leads to contemplation of spatial phenomena related to regional uniqueness. The comprehensive analysis of this problematic implies the use of the variety of sources for studying the specificity of architecture of particular cities, issues regarding the establishment of urban space, its transformation, changes in sociocultural situation, and other aspects. Semiotics as the methodology for studying architectural space serves as foundation for the analysis. For the first time, from the perspective of semiotic approach, the author analyzes the architecture of Crimean cities in the context of the uniqueness of cultural landscape of the Crimean Peninsula, which carries certain information enclosed within sign system. Y. M. Lotman’s theory of semiosphere alongside V. L. Kagansky’s concept of landscape hermeneutic, viewed in the context of regional specificities, underlie the analysis of the indicated cultural landscape. The research reflects a new approach towards studying the Crimean urban space as the cultural landscape, based on the sociocultural problematic of modern urban studies. City is interpreted as a social phenomenon, characteristic with system symbols, perception of which changes dynamically due to ongoing processes in the Crimean Peninsula.