Experiential Education is an educational approach not primarily concerned with knowledge acquisition but focusing on the training of behavioural skills in order to increase social and personal competencies in its participants. While the roots of this approach can be traced back as far as the philosophers of ancient Greece, it is currently experiencing a wave of mainstream popularity, due to its proven success. Adventure initiative games are a form of intervention frequently applied in experiential education settings in order to promote and refine social and personal skills. Some key elements of this game category are presented along with explanations on how they integrate virtual worlds to enhance creativity and engagement in the players. It is argued that for educational as well as evaluation purposes, it appears valuable to augment initiative games through mobile digital devices. A suggestion for a game design including specific details as well as an evaluation procedure is presented. Thus, the chapter aims to merge a theoretical contribution from the field of computing with practical considerations of a trained pedagogue and educational field researcher.