Saewulf’s Relatio de situ Jerusalem is one of the most significant yet understudied pilgrim texts of the twelfth century. Documenting the Jerusalem-bound traveler’s adventures through the medieval Mediterranean, the text is the first extant pilgrim document written immediately after Latin Christian armies seized control of the holy city. This article examines the text’s remarkable interest in autobiography and explores the resonance which crusading, early crusading narrative, Islamic presence, and Mediterranean voyaging had upon the pilgrim genre. This new analysis of Saewulf’s pre-modern self-fashioning is crucial to ways in which literary historians assess pilgrim literature through the valuable anthropological theories advanced by Edith and Victor Turner. As argued here, the status of a militarized Mediterranean in the twelfth century led to a shift in how pilgrims wrote about themselves. Saewulf positioned himself as a pilgrim who is transformed by his vivid exploits, not at the locality of the shrine, but while en route to Jerusalem. This study is an intervention in pilgrim and travel theory, proposing 1104 as a watershed moment in medieval travelers’ self-perception and autobiographical portrayal.