The last years witnessed a growing number of devices that track moving objects: personal GPS equipped devices and GSM mobile phones, vehicles or other sensors from the Internet of Things but also the location data deriving from the Social Networks check-ins. These mobility data are represented as trajectories, recording the sequence of locations of the moving object. However, these sequences only represent the raw location data and they need to be semantically enriched to be meaningful in the analysis tasks and to support a deep understanding of the movement behavior. Another unprecedented global space that is also growing at a fast pace is the Web of Data, thanks to the emergence of the Linked Data initiative. These freely available semantic rich datasets provide a novel way to enhance trajectory data. This thesis presents a contribution to the many challenges that arise from this scenario. First, it investigates how trajectory data may benefit from the Linked Data Initiative by guiding the whole trajectory enrichment process with the use of external datasets. Then, it addresses the pivotal topic of the similarity computation between Linked Data entities with the final objective of computing the similarity between semantically enriched trajectories. The novelty of our approach is that the thesis considers the relevant entity features as a ranked list. Finally, the thesis targets the computation of the similarity between enriched trajectories by comparing the similarity of the Linked Data entities that represent the enriched trajectories.