Background: This article examined intervention studies that used appreciation of visual arts to foster observation skills and discussed their effectiveness in making accurate diagnoses in terms of expertization. Methods: In order to collect journal articles and academic books (written in English) on empirical intervention studies that examined the use of visual arts for cultivating observation skills in health professionals’ education and training, the author first targeted articles that had been included in previous systematic reviews. In addition, they conducted a manual search. From this body of literature, the author selected studies that objectively measured observation skills only through the appreciation of visual art. They collected and read around 300 articles and selected 12 studies after applying the inclusion and exclusion criteria. Results: This article revealed no concrete evidence on whether appreciating visual art contributes toward an accurate diagnosis. Extant studies determined that such appreciation facilitates the observation of more visual features and a detailed view over time. However, they did not confirm the positive effects of appreciating visual arts on an accurate diagnosis. This article also confirmed that such appreciation does not reduce misdiagnoses or develop tolerance toward ambiguity that prevents premature closure. Moreover, the transfer of observation skills from one context to another is unlikely to be as successful as the intervention studies had intended. Conclusions: For fostering diagnostic skills, providing students with many instances of medical cases and appropriate knowledge to evoke implicit learning for extracting subtle differences in the cases, should be prioritized over visual art appreciation. On the other hand, such appreciation may foster verbalization skills and understanding or extraction of the patient’s background and context. These competencies may cultivate teamwork and perspective-taking, indirectly leading to an accurate diagnosis.