Recent archaeological evidence from Cyprus shows that humans first arrived on the island at around 12,000 calibrated years BP. Visits to Cyprus intensified and resulted in settlement of the island during the Pre-Pottery Neolithic A beginning around 11,000 cal BP. Later occupations of the Cypro Pre Pottery Neolithic B from around 10,500 to 9000 cal BP are more numerous and testify to intensive connections with the mainland. Cyprus as an island could have been reached only by seafaring. We examined the possible routes for sailing from the mainland to Cyprus and back to better understand the relationship between the island and the mainland during these periods. The factors that were examined were: sea level; options of available watercraft; sea conditions and currents; navigational skills; sailing routes; and prevailing seasonal and diurnal wind regimes. Because the present wind pattern is understood to generally resemble that of the Terminal Pleistocene pattern, it is suggested that the optimal sailing route and season from the mainland to Cyprus by Neolithic navigators was from southern Turkey between April and October. A passage westward or northwestward from the Levant coast to the southern coast of Cyprus cannot be ruled out. Their return trip was from the east or southeast of Cyprus to the Levant coast. This counter-clockwise Neolithic sailing pattern to Cyprus enabled permanent human settlement of the island and contacts with the mainland.