As the birthplace of the Abrahamic religions, the Eastern Mediterranean has long fascinated the Orthodox Christians of Ethiopia. Beyond its identification as the ancestral home of the region’s Solomonic kings, the Holy Land has also been the source of a scriptural tradition, a powerful symbolic landscape, and a canon of “translateable” scholarly works. But in the nineteenth and twentieth centuries, imperial politics and sectarian tensions dramatically transformed these older ties between the Red Sea region and the Holy Land. This paper will chart Ethiopia’s changing imagination of Palestine, Israel, and Egypt through a range of Amharic and Ge’ez texts: after considering their place in manuscripts of classical church learning, we will juxtapose these with printed works from the 1920s that investigate the region as a contested political space and a diasporic national home. We will conclude by proposing some links between this Ethiopian imaginary and missionary representations of the Holy Land from the same period.