Sensing passersby and detecting crowded locations is a growing area of research and development in the last decades. The COVID-19 pandemic compelled authorities and public and private institutions to monitor access and occupancy of crowded spaces. This work addresses the detection of crowds in points of interest (POI) by using a territory grid analysis categorizing POIs by the services available in each location and comparing data gathered from a community passive Wi-Fi infrastructure against mobile cellular tower association data from telecom companies. In Madeira islands (Portugal), we used data from the telecom provider NOS for the timespan of 4 months as ground truth and found a strong correlation with sparse passive Wi-Fi. An official regional mobile application shows the occupancy data to end-users based on the territory categorization and the passive Wi-Fi infrastructure in POIs. Occupancy data shows historical hourly trends of each location, and the real-time occupation, helping visitors and locals plan their commutes better to avoid crowded spaces.