The article revisits one of the grand initiatives of the admiral and reformer, Grand Duke Constantine Nikolaevich – the “literary expedition” sponsored by the Navy Ministry in 1855−1861. The author specifically problematizes the views of Russia’s civilizing mission as expressed by participating writers, who were commissioned to explore the empire’s diverse littoral populations – the potential resource of sailors. Focusing on the ethnographic essays penned by expedition participants such as Aleksei Pisemskii, Apollon Maikov, Mikhail Mikhailov, Sergei Maksimov, and Ivan Goncharov, the author demonstrates that the problem was not those writers’ belief in Russia’s civilizing mission itself, but their understanding of the ultimate goal of “civilizing.” The majority (with the exception of Pisemskii) were inclined to advocate complete assimilation of ethnically non-Russian peoples. And all the participating writers tended to classify peoples of the empire along rigid cultural and even biological hierarchies, which suggests that the discourse of racialization had already revealed itself in Russia by the 1850s. The author substantiates this claim by placing the views of writers− expedition participants within the broad historical context of ethnography and Oriental Studies of the mid-nineteenth century.