This dissertation research project focuses on maritime exploration during the Age of Discovery and the vessels that were the technological impetus for this dynamic era that ultimately led Christopher Columbus to the New World and Vasco da Gama to India. Little is known about the caravel and the nau, two ships which defined this era of global expansion; archival documents provide scant information regarding these vessels and to date there are only a few known archaeological examples. The caravel and the nau became lasting symbols of the bourgeoning Portuguese and Spanish maritime empires and are featured prominently in contemporaneous iconography. This dissertation bridges the gap between the humanities and sciences through the statistical analysis of the caravel, galleon, and nau in the iconographic record. As one of the first intensive uses of iconography in nautical archaeology, the study analyzed over 500 images using descriptive statistics and representational trends analysis in order to explore the two research questions posed, Are the ships represented in the iconography accurate? and Can iconography provide information on constructional characteristics of these vessels that will determine typology, evolution, and design changes? Gauging the accuracy of the ship representations was fundamental to establishing this study’s validity. The artists creating these images were not shipwrights or mariners and thus this research was not limited to the technological and constructional aspects alone. The dissertation addressed technology as a cultural symbol in order to understand how and why cultures attach such powerful and important symbolism to technology and adopt it as an identifying feature. On a broader level, this dissertation proved that iconography is a viable data source within nautical archaeology. The representational trends and general construction proportions analyzed in the iconographic record did provide an ample amount of information about the different ship types to greatly assist in the reconstruction of a caravel, galleon, or nau. The vast quantities of new data generated using these methodologies have the potential to significantly advance the study of these three ship types when paired with current and future archaeological evidence.