Pilgrimage to Jerusalem has been popular since at least the fourth century, and still attracts many Christians today. Throughout the history of pilgrimage to the Holy Land, a deep theological ambiguity has characterized the journey. Writings from the patristic period reveal a "teaching of restraint", contrasted by an enthusiastic endorsement of going on pilgrimage "to increase the grace of charity. " The present thesis examines the history of Christian pilgrimage to the land of the Bible and identifies a broad range of motivations and theological dilemmas. Pilgrimage is first seen in the context of the history of religions, as "worship in motion", an example of Eliade's "creative hermeneutic". Anthropological approaches, especially those of the Turners, are studied and critiqued. MacCannell's understanding of modern tourism as a "quest for the authentic", and Cohen's phenomenological study of the "existential tourist", provide points of reference for establishing the relationship between pilgrim and tourist. A qualitative study, based on "personal experience" interviews, provides the data for studying contemporary Christian pilgrimage to the Holy Land. The actual words of pilgrims about their motivations, the journey, their encounters, the shrines, and the return home, all reveal creative ambiguities of a theological nature. These are characteristic of a postmodern age, in which orthodox understandings of Revelation, Incarnation and Salvation are challenged and deconstructed. Personal pilgrim stories are evaluated in the present thesis in the light of narrative theology. Between Loughlin's "narrative orthodoxy" and Taylor's "erring", the pilgrim maps a path of faith through the uncertain terrain of postmodern religious experience. On a journey to contemporary Israel and Palestine, the pilgrim finds God "on the edge" and encounters Christ in the "other", especially in unscheduled encounters with Jews, Muslims and local Christians. This storied process of pilgrimage through both ambiguity and faith leaves traces of reform and renewal, to be developed theologically and practically when the pilgrim returns home.