In one of his first works, Topography of Ireland, Gerald of Wales describes his work as a “collection of the most curious facts”. At first glance, his writing appears to conform with the typical conventions of medieval travel narrative, describing new landscapes, flora and fauna, and people. Yet, what characterizes Gerald’s writing is the extent to which his personal ambitions, political biases, and internal identity conflicts pervade his narrations. Modern scholarship has generally viewed Gerald as a medieval ethnographer, or as a religious historian and writer. This paper instead argues his travel writings serve as a form of autobiography, in which his version of the truth functions as a form of self-representation. By analyzing Gerald’s most well-known works about his travels through Ireland and Wales through an autobiographical lens, this paper demonstrates how his personal motivations shaped not only his narrative style and subject matter, but also the image of himself he constructs within the text. Ultimately, this paper reconstructs the contemporary understanding of medieval travel narratives by reframing Gerald of Wales as an author interested in both observation and self-representation.