An information processing apparatus including: a display control unit configured to cause a first video to be displayed in a display area that a user visually recognizes, the first video being captured by a first imaging unit mounted on a first moving body that moves in a first space. The display control unit generates a first transition video corresponding to a viewpoint position that is moved continuously between a first viewpoint which is a viewpoint of the first imaging unit and a second viewpoint for imaging the first space.