Wildfires represent a natural phenomenon with detrimental effects on natural resources and human health. A better knowledge, perception, and awareness of wildfire risk may help communities at risk of exposure to prevent future events and safeguard their own lives. The aim of this study is to explore differences between individuals with and without previous wildfire experience, in terms of (1) subjective and advanced wildfire knowledge, (2) self-reported perceptions, (3) level of information, (4) self-protection measures, and (5) importance of community involvement. As a second step, we investigated differences in the same variables, focusing more deeply on a group of individuals with previous wildfire experience, classifying them according to fire-related employment (fire-related workers vs. non-workers) and wildland–urban interface (WUI) proximity (WUI residents vs. non-WUI residents). The Kruskal–Wallis test was applied to establish differences between the pairs of subsamples. Our results partially confirmed our hypothesis, that direct experience leads individuals to have a greater preparedness on the topic of wildfires. Perception of knowledge is reflected only at a shallow level of expertise, and, therefore, no relevant within-group differences related to fire-related employment or to WUI proximity were detected. Moreover, available information was perceived to be insufficient, thus we report a strong need for developing effective communication to high-risk groups, such as homeowners and fire-related workers.