The South Seas Project is a joint research venture between the Centre for Cross-Cultural Research, James Cook University and the National Library of Australia. It is focused on the creation of a web-based hypermedia edition of the journals and images documenting Cook's momentous first Pacific voyage (1768-71), together with annotations and essays in various media. The creation of such a complex artifact presents various intellectual conceptual and technical challenges. In this paper, I explore what seem to me some of the more important of these challenges, notably those relating to the cross-cultural nature of Australian and Pacific history. I also reflect on the problems associated with developing a digital information management and publication system that historians can use to engage in the critical practices they have traditionally undertaken and championed through the medium of print-based communication.