During the COVID-19 pandemic, social distancing measures were employed to contain its spread. This paper describes the deployment and testing of a passive Wi-Fi scanning system to help people keep track of crowded spaces, hence comply with social distancing measures. The system is based on passive Wi-Fi sensing to detect human presence in 93 locations around a medium-sized European Touristic Island. This data is then used in website plugins and a mobile application to inform citizens and tourists about the locations’ crowdedness with real-time and historical data. To understand how people react to this type of information, we deployed online questionnaires in situ to collect user insights regarding the usefulness, safety, and privacy concerns. Results show that users considered the occupancy data reported by the system as positively related to their perception. Furthermore, the public display of this data made them feel safer while travelling and planning their commute.