Drawing on auto-ethnographic descriptions from four decades of my own work as a Jewish guide for Christian Holy Land pilgrims, I examine how overlapping faiths are expressed in guide–group exchanges at Biblical sites on Evangelical pilgrimages. I outline several faith interactions: Between reading the Bible as an affirmation of Christian faith or as a legitimation of Israeli heritage, between commitments to missionary Evangelical Christianity and to Judaism, between Evangelical practice and those of other Christian groups at holy sites, and between faith-based certainties and scientific skepticism. These encounters are both limited and enabled by the frames of the pilgrimage: The environmental bubble of the guided tour, the Christian orientations and activities in the itinerary, and the power relations of hosts and guests. Yet, unplanned encounters with religious others in the charged Biblical landscape offer new opportunities for reflection on previously held truths and commitments. I conclude by suggesting that Holy Land guided pilgrimages may broaden religious horizons by offering an interreligious model of faith experience based on encounters with the other.