It has been verified that today in the Italian schools there are about 15-20% of students presenting different kinds of "Special Educational Needs". In order to respond to BES, the schools follow the Customized Learning Plan (PDP), a useful tool for designing operational models, strategies, systems and learning criteria for each student. For the various operators involved in the treatment of the disorders and also for the parents, it is of great importance to have adequate, efficient and flexible support tools that respect the desires and the enthusiasm of children of different age, without creating additional psychological and social discomfort. This research presents a particular relevance focus on the issue of management of entertainment and playful learning through digital systems offering a 'playful interaction'. New concepts of 'game' and 'device for interactive activities' offer screen-based compounds to scenarios on the relation between user and device, including physical activities or integrated physical gestures, which relate the observation of screen to the physical reality.