Women appear to have constituted the absolute majority of pilgrims to the Holy Land from the Russian Empire in the late nineteenth and early twentieth centuries. Several tens of them even became permanent or semi-permanent “pilgrims” in various locations of Syria-Palestine. By focusing on this latter group, I aim to examine some specific cases of the female experience of pilgrimage (business entrepreneurs, scribes or secretaries, nuns or crypto-nuns, and administrators’ wives). Further, I seek to analyze the ways in which male administrators and diplomats (both Russian and Greek, clergy and laymen) sought to counter, minimize or, ultimately, control the autonomous activity of these women. Utilizing correspondence sent to the Imperial Orthodox Palestine Society, and Russian and Greek diplomatic records, I wish to highlight the importance of autonomous female activity for understanding the gamut of the experience of pilgrimage from the Russian Empire in the Holy Land.