Education should not only seek to strengthen the intellect but should also aim to build character. In the Philippines, character education is an integral part of the curriculum. This study sought to contribute to the program’s pedagogical framework by advocating an experiential learning approach to character development, specifically in the cultivation of virtues. The Aristotelian concept of virtue development and the experiential approach to learning were the frameworks utilized to guide this study. The participants were thirty-five senior high school students at the University of the Philippines Visayas. The learning experience utilized was a one-month virtue challenge, wherein students were asked to identify virtues that they would want to start to cultivate within the context of their everyday life. An experiential learning reflection guide was used for their narratives which were thematically analyzed using an inductive method (Braun & Clarke, 2006). The data gathered included six virtues that the participants personally chose to cultivate, namely, thriftiness, industry, keeping healthy, self-reflection, joyfulness, and propriety, along with their corresponding activities; related virtues also emerged parallel to the six; challenges and strategies were also identified, and some key learning points.The study concluded that learning which included character development was a result of personal choice and that experiential learning was a necessary component in its process. Although the activity was classroom simulated, the experience and struggle were real; therefore, meaningful for the students.The study recommends for a pedagogical innovation in character education initiatives specifically in the creation of relevant learning spaces anchored on student reality.