Art-based observational training in museums has the potential to enhance observational and communicational skills and to augment competences as empathy and tolerance of ambiguity. We developed and implemented art- based observational courses for residents at three central surgical training centers in collaboration with major local museums. Groups of 6–12 residents participated in guided sessions in a museum led by an art historian and an experienced surgeon. The ABCD-method was used to structure layered examination and discussion of an artwork, supported by targeted exercises. Artworks were selected based on visual content and the possibility of depicted medical features for iconodiagnosis. Around 150 surgical residents participated in the program. The process of observing and interpreting artworks, exchanging reflections and debating visual physical abnormalities was highly valued. Works by famous masters such as Rembrandt, Rosselli, Rubens and Vermeer were examined and discussed from medical and art- historical perspectives. Herein, three works by Rosselli, Ket and Rembrandt, respectively, are reviewed in iconodiagnostic detail. Course design and group interaction not only showed educational value but also strengthened team cohesion. The synergy of observational training and iconodiagnosis in art-based settings enhanced the educational program. The courses were highly valued by the participating surgical residents and potentially improved their professional competencies. Our experiences support the integration of visual arts courses in surgical training. This approach may be applied in all medical disciplines.