In our increasingly complex and interactive world, it becomes ever more difficult to isolate and map the cultural identity of any given region, as bounded and contained cultural places have become a rare occurrence. To further complicate the matter, perspectives, loyalties, and identities shift with time, and appear to shift with circumstance. While cultural conflict per se was not the subject of this study, the ability to quantify differing cultural profiles in one location relative to another may be the beginning of the development of a tool for assessing degrees of difference in neighboring regions, and thus diagnosing the potential for conflict escalation. The Compass System, a holistic model that uses eight archetypal categories to observe and evaluate complex systems, was used for this study. In this exploratory study, 33 restaurants in 5 cities in Chile were rated in these eight categories as perceived by a team of outsider observers. The predominant qualities of each city sampled, determined solely from the sampling of its restaurants, did match, in a general sense, qualities of the city that were otherwise observable. This matching indicates that a tool such as the Compass System can be used to gather a collective regional profile from small sampling, such as an area’s restaurants. Potential uses for further research and development could include conflict management and assessing risk for social instability or escalation of violence.