One of the characteristics of the East African Coast has been its accessibility. The sea has been a means of contact with the outside world. Over the last 2000 years, there has been an interpenetration of cultures to this region through trade consequently assimilating this coast into the international economic system. Accessibility from the land has made the East African coast historically an integral part of Africa. This allowed movement of goods from inland to the coast and onward to international markets. This coast has a trade advantage because the monsoon winds and oceanic currents are reliable and permit rapid, seasonal navigation, both along the coast of eastern Africa and across the Indian Ocean to western and southern Asia. A number of scholars have discussed how the monsoon winds and currents facilitated communication between various parts of the Western Indian Ocean (WIO) seaboard and the Red sea, the Persian Gulf, and southeastern Asia. These winds caused long distance seasonal sailing along the East African coast and beyond to the rest of the ancient world. The islands of Comoros and Madagascar were also part of the Western Indian Ocean seaboard cultural and trade networks from very early times even before the BC/AD changeover. One of the major ancient coastal cities that played a role in this transoceanic trade is Mombasa in the Kenya coast. This paper explores these ancient trade contacts which have been proven by historical period stone anchors discovered in Mombasa, Kenya.