We report on a playful introduction of optimization in a high school. The final event of this experience has been an orienteering competition, in which the decision-making component plays a central role. This type of event has been very involving, and it boosted the interest of the students toward operations research. After summarizing the activities in class that preceded the competition, we describe in detail the organization aspects and the outcome. We also provide a simple AMPL code that compares the choices made by the participants with their optimal trajectory, that is, the one maximizing the score with the same traveled distance.