The article tackles the issue of Leo Tolstoy's attitude towards the city, perceivedas a sui generis organised space affecting behaviour of human beings. It analyses the literaryworks by the author of Anna Karenina, which either conjure up urban images or set their scenes in cities. Literary evocations are confronted with Tolstoy's non-fictional works and his own view on cities. The images of cities in Tolstoy are read by means of the apparatus typical of urban semiotics, developed mostly in the works by Yuri Lotman and Vladimir Toporov. In this paper, basing on Tolstoy's works, images of Western cities are confronted with thoseof Russian ones, with a special emphasis put on the writer's private opinion on city as humanenvironment. Tolstoyan vision of Saint Petersburg is analysed with regard to poetics of "thePetersburg text of Russian Culture". The article also hints at Tolstoy's inclination towards Rousseau's view on urban spaces.