Chekhov often said that ‘I am a doctor by trade and sometimes I do literary work in my free time’, a surprising claim, given his status as a giant of 20th century drama. This literary-biographical study uncovers new sides to him, as both a medical professional and humanitarian, and tells the story of Chekhov's trip to Sakhalin Island in the harsh wastes of Siberia. Anton Chekhov practiced medicine for most of his life and engaged in humanitarian work which took him away from writing for months. He placed one such trip though, across the unforgiving terrain of Siberia to write about the penal island of Sakhalin, above all others. Chekhov's Sakhalin Journey, written by a neuroscientist and practicing clinician, uses this trip and Chekhov's own account of it to shed light on hitherto overlooked aspects of his life. In doing so, it shows that to understand the man we need his medicine as well as his literature, and we need to assess his life from his perspective as well as ours.