Transformative travel has been a hot topic in tourism research in the last few years. To better comprehend this process, it is important to investigate how the tourist transformation happens during a travel experience, not only after the trip. This qualitative phenomenological study aims to understand transformative tourism experiences and how they happen during tourism experiences. Based on Mezirow’s transformative learning theory, tourism scholars investigated the transformative potential of tourism. The convenience sample adopted in this research presents a unique opportunity to assess tourists’ perceptions longitudinally. Travel motivations, on-site perception through dairy notes, and semi-structured interviews were used in this research design to in different times the travel experience. Results suggest that prior transformative tourism experiences can affect future expectations of transformation. Novelty, stimulations of some planned activities can contribute to perspective change during the trip different from what previous research indicated.