This paper presents “DESMOS”, a novel ecosystem for the interconnection of smart infrastructures, mobile and wearable devices, and applications, to provide a secure environment for visitors and tourists. The presented solution brings together state-of-the-art IoT technologies, crowdsourcing, localization through BLE, and semantic reasoning, following a privacy and security-by-design approach to ensure data anonymization and protection. Despite the COVID-19 pandemic, the solution was tested, validated, and evaluated via two pilots in almost real settings—involving a fewer density of people than planned—in Trikala, Thessaly, Greece. The results and findings support that the presented solutions can provide successful emergency reporting, crowdsourcing, and localization via BLE. However, these results also prompt for improvements in the user interface expressiveness, the application’s effectiveness and accuracy, as well as evaluation in real, overcrowded conditions. The main contribution of this paper is to report on the progress made and to showcase how all these technological solutions can be integrated and applied in realistic and practical scenarios, for the safety and privacy of visitors and tourists