What can Christopher Columbus’ experiences in the Bahamas teach us about Alexander the Great’s campaigns in India? This talk will consider the universal question of how conquerors and colonisers first engage with their new surroundings. How much do they listen to local people? How much do they ignore? We shall look at the two expeditions through the lens of indigenous guides, a relatively neglected topic in ancient Greek history. We shall explore whether and how modern historical settings — like Columbus’ voyages — can shed new light on ancient evidence. This talk serves as an introduction to my research on indigenous guides in Greco-Roman historiography and ancient Mediterranean history, which I am carrying out as Postdoctoral Fellow at the Haifa Center for Mediterranean History. While not explicitly dealing with the Mediterranean, this presentation’s methodological approach will be central to the wider project and has significant ramifications for our evaluation of Mediterranean history.