The modern educational theory, policy and practice share the dominant interest for the formal learning contexts. However, if learning is defined as a transformation of participation in socio-cultural activities within the community, all learning situations become significant. This includes the learning contexts beyond the formal school environment, e.g. informal learning. If learning is defined as a dynamic, undetermined, contextual social construction, responsible for person's transformation but also for modifying the context of learning, various kinds of informal learning situations should be brought into focus. In the present paper, the relationship between learning in two contexts, formal and informal, is investigated. The most relevant aspects of these teachings/learning processes were compared with respect to their potentials and limitations in preparing the developing person for full participation in the society. Since each person transmits all of his/her experiences through learning contexts, the boundaries between these learning environments are not so clear and stable from the perspective of the one who learns. On the other hand, the boundaries are more visible and relevant for different providers of teaching practice. In the second part of the paper, we proposed some directions as to how to bridge the two contexts of learning effectively and in a planned way.