This article examines the cultural and artistic context of one of the most famous Roman frescoes, the Odyssey Landscapes. It argues that the painting’s fictive portico frame would have evoked in the Roman viewer the experience of the ambulatio, the act of walking for leisure and contemplation that came to be an essential element of a properly Hellenized otium. The painted portico thus puts the viewers in the proper frame of mind to appreciate the intellectual associations of the painting as they walk with Odysseus on a parallel journey of philosophical reflection.