We present Tripmentor, a novel project, that is related to tourism in the region of Attica. The project has as main scope to provide rich media content to tourists through a web and mobile environment in two languages trying to guide them through alternative routes that include places of interest as well as organizations with offers to tourists. The project interconnects people with places and events in an automated manner trying to personalize on each tourist’s personality. The challenges of the project are mainly technological as through the processes of the project a) automated information about venues must be collected, b) information about events related to venues must be fetched and finally c) data related to system users and mainly their profile should be discovered and created in order to offer a unique experience to each of them. We present the scope of the project as well as the challenges of its implementation.