This comparative study of Italian medieval pilgrim’s journals and Russian khozheniya (medieval travelogues) shows, on the one hand, their genre similarities. They have comparable practical information: indication of route, distances, time and means of travel; comparable description of holy places and objects; and comparable accounts of local customs, natural environment, adventures and dangers. They are also written in similar styles, combining a documentary approach with religious emotion. On the other hand, the article demonstrates the differences in the perception of reality by Western and Russian pilgrims: the former are more rational and take as much interest in the secular world as in spiritual matters; the latter focus more on the inner experience of the encounter with the sacred and on recognition of their own sinfulness. European pilgrims are more open to the world, while their Russian counterparts look inwards into their hearts, where they seek to meet God. Such differences result from the contrasting historical and spiritual contexts of the authors’ lives.