We investigate a novel approach to e-Learning using Seman-tic Web technologies and aiming to optimise the learners’ experience incorporating pedagogical strategies into the learning process. The in-creasing availability of Semantic Web based educational resources and the establishment of open metadata standards like IEEE LOM pave the way for enhanced e-Learning systems that support personalised learning based on a reasoning framework and formal ontologies. We use ontologies to describe learning objects and the learner state, and define pedagogi-cal recommendation axioms that specify which learning objects are best suited for the learner in a specific situation. Recent pedagogical findings suggest that the individual learning can be optimised by means of guid-ance through learning pathways, i. e., a particular order in which learning objects are to be studied. To this end, we offer an OWL model for learn-ing pathways as structured sequences. We show the strengths and limits of OWL and propose a solution to overcome problems such as handling of soft constraints and ranking of result sets. The calculation for ranking is based on individual weights for specific learner-related features and considers the degree of match between learning objects and learner’s needs. The feasibility of our approach is shown by modelling real-life course material, i.e. a complete course on the Philosophy of Didactics. We implemented our approach as a prototype system and interfaced it to a standard Learning Management System.