Issues relevant to web-based communities in the Pacific Islands are described. A brief geographic and demographic overview is provided, and unique cultural, social and educational challenges are discussed, with particular attention to Hawaii, American Samoa, and Chuuk, Federated States of Micronesia as illustrative cases. The computer and allied web-based technologies are viewed as serving some of the same contemporary functions for voyagers as did the canoe, in the historical voyaging tradition. Projects that aim to address some of the educational and social needs of Pacific Islanders as voyagers at the University of Hawaii and as leaders in their home communities are presented.