The purpose of this study is to understand the development process and context of a coincidence experience that provides pleasure and meaning in travel. The in-depth interviews of 11 participants and data were analyzed using grounded theory. As a result, people who experienced coincidence in the trip were either on an impromptu trip without planning or with flexibly changing the schedule, or traveling alone. Participants experienced a coincidence while attempting to be tense and various trial and error at first, as they were placed in a somewhat uncertain environment through improvised travel and traveling alone. The central phenomenon – coincidence - is a form of synchronicity in which multiple events encounter at the same time, or it appears as a seriality in which the same event occurs repeatedly. After experiencing the coincidence, people were wondering if the coincidence was caused by someone's intention and an emotional reactions such as admiration and joy emerged only through the conviction that no specific cause was found, or that it was not the intention of someone, or the result of giving meaning such as memories or moments of growth. This suggests that people were experiencing coincidences in the process of creating uncertain situations through trips, overcoming tensions and anxieties, and challenging themselves. The coincidence provided existential authenticity to travelers, which allowed people to experience a series of happiness.