Increasingly, medical educators integrate art-viewing into curricular interventions that teach clinical observation—often with local art museum educators. How can cross-disciplinary collaborators explicitly connect the skills learned in the art museum with those used at the bedside? One approach is for educators to align their pedagogical approach using similar teaching methods in the separate contexts of the galleries and the clinic. We describe two linked pedagogical exercises—Visual Thinking Strategies (VTS) in the museum galleries and observation at the bedside—from “Training the Eye: (...) Improving the Art of Physical Diagnosis,” an elective museum-based course at Harvard Medical School. It is our opinion that while strategic interactions with the visual arts can improve skills, it is essential for students to apply them in a clinical context with faculty support—requiring educators across disciplines to learn from one another. (shrink)