Feodor Alekseyev, a leading representative of the genre of perspective cityscapes in the Russian academic art at the turn of the 18th century, combined artistic work and teaching practice for many years, simultaneously acting as the head of the workshop and the professor of the perspective painting class at the Imperial Academy of Arts. Based on Alekseyev’s activities, the author examines the content of the concepts of “workshop” and “school” in the era of classicism in Russia, when the earlier forms of master and apprentices’ working in a guild coexisted with the new academic system of training professional artists. The basis for the analysis was Alekseyev’s practical work commissioned by the Emperor, i.e. his execution of the views of Moscow, whose image symbolized national historical traditions and acted as a certain antithesis to the metropolitan Petersburg in the late 18th and early 19th centuries. The features characterising the relationship between the master and his assistants are reflected in Alekseyev’s collaboration with the graduates of the Academy, A.M. Kunavin and I.V. Moshkov, as they worked jointly on the graphic views of Moscow in 1800–1801 (after the business trip to the ancient capital on assignment for the Academy of Arts). The study of the paintings from the perspective of the typological features of images, their style and manner of execution let the author identify the respective roles of the master and his mentees in the process of creating the cityscapes. The article traces the compositional and semantic transformation of the views starting with watercolour drawings from nature and ending with the paintings that brought Alekseyev the glory of the first master of the Russian cityscape. Alekseyev’s experience as the head of the workshop, when he directly shared his expertise with his apprentices and determined the final result of their work, was extended in the activities of Alekseyev as a professor, who headed the class of perspective painting at the Academy of Arts from 1803 to 1824, and continued the practice of creating the panoramic views of Moscow. Thanks to the close integration of artistic and pedagogical practice, Alekseyev had a significant impact on the formation of the typological and figurative “model” of the urban landscape which was developed in the Russian art at the beginning of the nineteenth century.