In recent years, the popularity of hiking has steadily increased across different segments of the population. Although there is considerable evidence of the benefits for hikers regarding physical and mental health, the inherent risks of these outdoor activities cannot be underestimated. Accident prevention and an increase of awareness about possible risks are necessary to minimize hiking and pedestrian tourism’s negative consequences. In most hiking information maps and interactive applications, there is usually not enough information about difficulty points or the granularity level required to provide tailored recommendations to hikers with physical or psychological limitations. In this paper, we present Syris, a geo-information system for hiking itineraries that incorporates Points-Of-Difficulty to assess the level of effort, technique, and risk of hiking trails. The system allows users to filter itineraries and obtain recommendations based on the assessment of difficulty following a well-established methodology. The system has been implemented, deployed and tested with real data in the region of Val d’Anniviers in Switzerland, and is openly available to enable further developments and refinement.