Working holiday is different to common travel patterns. The participants are working in foreign countries. They not only need to contact with foreign residents, but also need to work together with the other participants from variety of countries. These cause participants may have deeply feeling of anxiety and uncertainty. Participants’ personality and risk perception therefore have great influence on their willingness of participation. This study aimed to realize Taiwanese youths’ willingness of participation of USA Work and Travel Program under different personalities and different risk perception. The participants of the USA Work and Travel Program should be 18 to 28 year-old students. Thus, for research convenience, the students of Chinese Cultural University were chose as the research samples. After analyzing 570 questionnaires, it was proved that personalities significantly influence youths’ willingness of participation as well as their risk perception of working holiday. In addition, higher risk perception will cause lower willingness of participation. This study suggest youths who plan to be working holiday makers and the institutions which hold working holidays to realize youths’ personality in advance, in order to have good working holiday experience.