Much criticism has emphasized how travel is to be conceptualized in terms of mobility. This essy, however, argues that such viiews neglect the spiritual component of the dialectic of travel in the medieval West, which envisions an alternative traveling of the mind: inner journeying. Drawing on the discourse of emotion, I argue that inner journeying is a highly laborious task that requires those who cannot be on the road to actively channel compassion and experience the travail of travel as a form of emotional labor—a self-imposed, affective realignment with the suffering of Christ. Using the thirteenth-century Middle English monastic manual Ancrene Wisse as its focus, this essay demonstrates that not only is the anchoress’s practice of compassion contextualized via the rhetoric of place pilgrimage, but it is also deemed the most desirable form of travel. Through the act of immersion into the body of the suffering Christ and the reproduction of the emotional experience of the Passion, the anchoress is thus envisaged as a traveler-pilgrim whose emotional toil helps her reach a virtual synchrony with Christ ions.