Spectral imaging of Portolan Charts, early nautical charts, provided extensive new information about their construction and creation. The origins of the portolan chart style have been a continual source of perplexity to numerous generations of cartographic historians. The spectral imaging system utilized incorporates a 50 megapixel mono-chrome camera with light emitting diode (LED) illumination panels that cover the range from 365 nm to 1050 nm to capture visible and non-visible information. There is little known about how portolan charts evolved, and what influenced their creation. These early nautical charts began as working navigational tools of medieval mariners, initially made in the 1300s in Italy, Portugal and Spain; however the origin and development of the portolan chart remained shrouded in mystery. Questions about these early navigational charts included whether colorants were commensurate with the time period and geographical location, and if different, did that give insight into trade routes, or possible later additions to the charts? For example; spectral data showed the red pigment on both the 1320 portolan chart and the 1565 Galapagos Islands matched vermillion, an opaque red pigment used since antiquity. The construction of these charts was also of great interest. Spectral imaging with a range of illumination modes revealed the presence of a “hidden circle” often referred to in relation to their construction. This paper will present in-depth analysis of how spectral imaging of the Portolans revealed similarities and differences, new hidden information and shed new light on construction and composition.