I begin by considering first imagination in the first Kantian Critique as an active function of sensibility, and then examine its role in serving the understanding, before analasying its involuntary play which generates fantasy, daydreams and illusion, and which poses the problem of controlling our power of imagination. Then I consider the interplay between imagination and ideas of reason, note that for Kant reason forms an idea as a focus imaginarius, highlighting both the illusory and the regulative sides of their relationship. With these roles in view, I finally turn to appreciate the immanent role played by imagination in the ‘adventures’ of reason, illustrated by Kant through a maritime metaphor, whose historical-geographical sources will be disclosed.