This chapter charts the history of the principal Red-Sea ports connecting to the Egyptian Nile in the medieval period: al-Qulzum, Quseir and ‘Aydhab. Al-Qulzum, at modern Suez, was for a time at the mouth of a Nile-Red Sea canal, and also served the relatively short overland crossings to Cairo/Fustat and the Mediterranean at al-Farama. ‘Aydhab, at the southern extreme of Egyptian influence, flourished particularly during the Fatimid era as a port serving Arabia and Indian Ocean connections, despite the long overland journey to and from the Nile. Quseir, at the closest point in Upper Egypt between Nile and Red Sea, came to prominence in the Ayyubid and Mamluk eras. The chapter examines the navigational advantages and disadvantages of each location, and compares these with the chronology of their respective prosperities. It concludes that geo-politics, rather than navigational considerations, prevailed in the use of these ports in the medieval period.