The year 2022 marks the 350th anniversary of the birth of the leader of the first Ukrainian emigration in Europe, hetman Pylyp Orlyk (1672–1742). The main goal of this article is to present an analysis of a certain manuscript which was first read out loud and prepared for publication in 1724. It contains a fragment of a diary that Orlyk wrote during 1720–1732. The year 1724 was one of the hardest in his travels through the Turkish-occupied province of Thessaloniki, where an epidemic (or, as Orlyk put it, “infection,” “evil air” or the “plague”) that lasted for several years broke out. Orlyk’s diary of subsequent years, including 1730, is filled with dramatic imagery of the disease. The article uses the methodology of the history of private life. The author explores the motifs of both miraculous and real recovery. In the conditions of isolation, enforced loneliness, the separation from his wife, Anna Gertsik, and their eight children, Orlyk finds salvation in his faith in God, but also in reading, translating, learning foreign languages, and communicating with a few friends. The author comes to the conclusion that Orlyk resembles Montaigne in his understanding of loneliness. What he seeks is not isolation from people, but inner freedom, and he strives to reunite with his family.