There has been a lot of discussion recently about visiting the Holy Land (Israel), especially among those who believe in Jesus Christ. This paper qualitatively reviews the historical background of the Holy Land, introduces why people like to visit Israel, and looks at the religious and cultural affairs of the Jewish people. Specifically, this paper identifies and discusses five reasons for travelling to the Holy Land: (1) leisure; (2) pilgrimage; (3) experiential; (4) diversionary; and (5) experimental. The research methodology will look into the web statistical survey of 102 interviewees, as well as the documentary analysis of churches visited in Israel, among others. Qualitative analysis will then be used to determine the barriers to Christians’ deciding to visit the Holy Land. One of the main focuses of the paper is the relationship between faith and feeling secure in the Middle East due to the current tensions between Islamic countries and Israel. This faith–security connection will be investigated to determine a new type of Christian typology for travellers to the Holy Land a mix of curiosity, depression (or anxiety), and desire for pilgrimage that disproves Erik Cohen’s tourism model. Specifically, how faith overcomes feelings of anxiety in terms of security, thereby creating a corresponding experience. By determining that the motivation for travelling to the Holy Land for these types of Christians is out of curiosity (e.g., wanting to visit the birthplace of Christianity, concern regarding the on-going Israeli–Islamic conflict, desire for spiritual pilgrimage, etc.), one should be able to further deduce the role that faith plays in their final decision outcome. Finally, this paper empirically creates a Markov decision process model which lays the groundwork for future research.