Through an analysis of three sets of historical documents concerning population drifting and movements, this paper intends to explore the likely ethnic contact and cultural affinity between Yona-guni island, Yaeyama Archipelago and Taiwan during the period between late 15th century and early 19th century. Using evidences from the first set of documents, witness accounts given by some Koreans from Cheju island who had drifted on the sea to Yonaguni ls. and Ryukyu Archipelago, I will maintain that there were significant similarities between the eastern coast of Taiwan and Yaeyama Archipelago with respect to subsistence technology, social institution, and agricultural system. With some portions of the official chronologies of Yaeyama Archipelago, the second set of documents I utilized, I will demonstrate that the relations between Yaeyama Archipelago and Taiwan were rather amiable and in 17th and early 18th century, a situation making it possible for Taiwan to serve as a haven for refugees and drifters. The third set of documents, consisting of regulations made by the Yaeyama Archipelago, government to curb smuggling activities by "Tang" ships, indicates that the relations between the two areas were tense at the time. This paper attempts to show that whether through accidental drifting or purposeful population movements through the area comprising Taiwan and the islands to its east, various kinds of trans-national socio-cultual interflow are likely to occur. 1 conclude by arguing that it is an urgent task to reconstruct the ethnohistory of eastern Taiwan and the neighboring islands.