Direct student experience of the real, live organism, object, place or environment is recognised by teachers and other educators as having powerful potential for high quality learning. Rendering this rich experience into explicit learning contexts for students remains an on-going pedagogical challenge. The use of mobile technologies as a way for students to capture their experience as it happens in the real world holds great promise as a vehicle to support authentic learning. This chapter presents a series of cases where different school groups were challenged with different mobile learning activities. The first two cases are derived from research studies in the local environment. In these two cases students were involved in inquiry-based learning where they used data collected in the field with handheld computer and digital cameras to assess the health of their local environment. The second two cases are derived from complementary geography tasks in the field. In one case students worked in pairs to navigate a given route, and in the fourth engaged in a debate about an issue pertaining to urban planning using text- and picture- messaging technologies. The results of the cases are analysed with a view to generating some general principles around the technologies, the activities and the tools that comprise the pedagogies embodied in these cases. It is hoped that they will inform more effective professional practice, specifically when teaching spatially dependent tasks and, more generally, in mobile collaborative learning environments.