Transformative experiences are meaningful encounters that have the potential to change the attitude and behaviour of the participants. Whilst, there is a wide array of theoretical perspectives that have been used to explain the processes and triggering factors of the tourist transformative experience, this chapter proposes a liminality and immersion perspective. This perspective provide a more holistic understanding and shows that transformative experience is an on-going process that extend from the pre-liminal, liminal and post-liminal phase and facilitated by deep engagement in the activities. It is also argued that the experience and transition to the liminal world is largely facilitated by contextual elements such as; physical environment; social dynamics and thematization around a story. Likewise, psychological factors such as the tourists’ motivation, level of readiness and openness to learn and personal characteristics of the tourists are vital. Altogether, both the contextual and psychological contribute in triggering change in behaviours.