The aim of this paper is to open up the typological parallelisms (motives, colours, and the position of the lyrical “me”) between the city imageries of Rilke and Blok. The analysis covers Rilke’s lyrics and Blok’s three cycles (The City, Terrible World and Italian Verses). The comparative analysis focuses on the poetry of their hometowns (Prague and St. Petersburg), that of modern cities, and of Italian towns visited by the authors. The question of the modern city and the criticism of civilization represent several similarities in the two poets’ works, but the secessionist garden, park, and castle motives occur only in Rilke’s poetry. The topics of Venice and St. Petersburg, which are related to each other in many ways, are formulated in the objective lyrics of Rilke’s volume New Poems. In Blok’s poetry, it is the composition and the philosophical content of the Italian Verses cycle as a high-ranking and complete literary work that deserves special attention.