The advanced cognitive capability of Homo sapiens significantly facilitated their adaptability to a wide range of environments during their dispersal out of Africa during the Late Middle Pleistocene. In this matter, marine environments with their dense concentrations of fauna, rich in fatty acid nutrients, are thought to have been important in subsistence. By at least 65,000 BP, H. sapiens dispersal from Asia to Australia involved the first known significant period of human maritime adaptation, which would have required open water crossings via the insular Wallacean archipelago. However, despite the undoubtable knowledge of nautical skills, no strong direct evidence of open seafaring has been discovered so far. Here, we discuss the results obtained through the analysis of ichthyoarchaeological assemblages from several sites dated from the Late Pleistocene to the mid-Holocene in the Philippines and in the Lesser Sunda Islands. By including them in a broader perspective and taking into account previously published studies in Sulawesi (Indonesia) and Okinawa (Japan), we highlight a north-south difference in cultural adaptation to the environment. On all the studied sites, fishing was only practiced from the shoreline or near the coast. While the assemblages discovered on most in the Philippines reflect occasional fishing, the southern sites in the Lesser Sundas show evidence of marine specialization with the development of techniques adapted to each type of environment surrounding the sites. Marine resources were well managed. Offshore fishing was probably not necessary, as its practice would have led to unnecessary risk taking. However, this specialization would require the development of efficient technologies and a strong cultural transmission across generations. This study provides insights into the colonization of the Pacific by Homo sapiens and perhaps some new tools to aid in our understanding of the preferred colonisation route through Sahul: the northern or southern route.