Technologies are changing the way we teach and learn in many respects. A relevant and not yet fully explored aspect is that they can support, even entice, students and teachers to go beyond the school boundaries, in spatial and temporal terms. Teachers and learners can keep in touch and work together, when they are not at school; they can access "the world" via Internet; peer to peer remote cooperation is possible; multimedia possibilities provide an incentive to explore the territory, the features of which can be documented in an effective way; digital content can be accessed, created, refined at any moment, at school and from home. This paper discusses this issue at the light of PoliCultura, a large-scale (20,000 users) digital storytelling initiative at the borders between formal and informal education, in which students and teachers collaboratively create a multimedia story. In order to accomplish this task, they interview experts, visit local institutions, involve their families and the community at large, cooperate through social media with remote peers, working at school as well as from home: in other words, they go "beyond the school's boundaries." In doing so, they not only get engaged but they achieve substantial educational benefits.