Western Europeans (fifteenth–sixteenth century) travelled to Southeastern Greece and the Mediterranean by land or sea for various purposes, such us commerce, pilgrimage to the Holy Land or diplomatic missions. Erudite Italian humanists interested in antiquity toured the Greek islands and partly explored continental Greece. They recorded their journeys in the early travelogues. Travellers with a certain theoretical baggage recount the historical past, drawing upon Greek and Latin literature, as well as their personal experiences from their travels. The present paper focuses on the perception of nature and people, as presented in three different types of literary genres: an isolario, a diary and a narrative poem. Cristoforo Buondelmonti in his isolario Liber insularum archipelagi (1420), Ciriaco d’ Ancona in his Diaries from his early and later travels (1400–45), and Hugo Favolius in his epic poem Hodoeporici Byzantini libri III (1563) enrich their reminiscences of the classical past with representations of Greek nature and comments upon the people they encounter. This article aims to explore the varied approaches of the writers and the aspects of Greek nature and the local people, which are enhanced in their travel accounts.