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This paper provides comparative analysis of Petr Viazemskii’s Puteshestvie na Vostok (1849—1850) and Nikolai Gogol’s letters from 1848, reflecting writers’ pilgrimage to Jerusalem. Both Viazemskii and Gogol reflect on the Jewish presence in the Ottoman Empire and its policies towards religious minorities. Studying the patterns in describing Jewish inhabitants of the “Holy Land” by Russian noblemen provides better understanding of how the “Jewish question” was perceived in Russia of the last years of Nicholas I rule.