An endoscope insertion shape observation apparatus includes an insertion section configured to be inserted into a subject, and a processor that detects an insertion shape of the insertion section, generates an insertion shape image representing the insertion shape, generates a body outer shape image representing a body outer shape of the subject, and performs display control to simultaneously display the insertion shape image and the body outer shape image in a positional relationship corresponding to a positional relationship, in a body cavity of the subject, of the insertion section on a display screen. The display control also switches between display or non-display of the body outer shape image or a type of the body outer shape image depending on an insertion position, in the body cavity of the subject, of the insertion section.