Design, planning, and management of the urban soundscape require various interacting fields of knowledge given the fact that it is the human person that experiences and provides meaning to the urban places and their acoustic environments. The process of environmental perception involves contextual information that conditions people’s responses and outcomes through the relationship between the variables Person, Activity, and Place. This research focuses on the interaction between Person and Place and its impact on responses and outcomes from listeners with different geographical origin and background. Laboratory studies were conducted in the cities of Lisbon (Portugal) and Bogotá (Colombia), where local listeners were introduced to known and unknown acoustic environments. Sound data recorded in the two cities allowed comparison of responses and outcomes of the listeners according to the Person-Place Interaction, leading to different meanings depending on the contextual variables. The results clearly show a relationship between site, acoustic environment, soundscape, Person-Place Interaction, and meaning of the place. This information can be useful for urban technicians and designers dealing with planning and management of urban soundscapes.