There is provided a wearable medical observation apparatus used by being worn on a head of a user, including: a first observation section having a configuration enabling a first observation of an observation target through an optical system including at least an objective lens; a second observation section having a configuration enabling a second observation of an observation target by a first medical observation image in which the observation target is imaged by a first imaging device; and a control section configured to control an observation state of the observation target.