Wikis are currently in high demand in a large variety of fields, due to their simplicity and flexible nature. Documentation, reporting, project management, online glossaries and dictionaries, discussion groups, or information systems are just a few examples of possible Wiki applications. Their popularity has also begun drawing the attention of teachers and educators, who realize that Wikis facilitate collaborative finding, shaping, and sharing of knowledge, as well as communications, all of which are essential properties in an educational context. In order to leverage the possibilities that Wiki systems offer for didactic and interdisciplinary scenarios, this paper examines how Wiki functionality can be extended in order to better suit the requirements posed by such environments and their participants. A concept is suggested that allows building context and structure around the content and existing information organization, using trails, or paths, through the Wiki content. These can either be manually added by teachers and tutors, or inferred automatically through an integrated tracking mechanism that makes use of the implicit navigational information left behind by the users as they browse the Wiki. Finally, an actual implementation of the concept is presented and discussed, followed by an outlook on future developments and possible uses.