During the 14th and 15th centuries there was a significant resumption in the practice of the traditional “medieval” pilgrimage, by means of galleys and ships plying the Mediterranean Sea. Among the renaissance’s knights who travelled to the Holy Land was Konrad Grünenberg, a personality who is not very well known. In 1486 he embarked from Venice to Jerusalem. Konrad’s travel diary is one of the most beautiful examples of the genre, showing notable drawing skills, particularly in the illustrations of the coastlines of the main cities he encountered on his route to Palestine. Accompanying these views, Konrad reported on a wealth of interesting geographic and topographic details. Based on his previous architectural training, Konrad was also able to annotate his drawings with construction details of buildings, and indications of the shapes of the main urban settlements, particularly the configuration of harbour structures and fortifications.