An information processing apparatus includes: a map expression data storage unit in which two or more pieces of map expression data are stored; a position specifying information storage unit in which one or more pieces of position specifying information are stored in association with the map expression data; a request instruction receiving unit that receives a request instruction containing specifying information for specifying map expression data, from a terminal apparatus; a data acquiring unit that acquires map user information having map user information specified with the specifying information, and one or more pieces of position specifying information associated with the map user information; and a transmitting unit that transmits position added map expression data in which a position specified with the map user information, or the position specifying information contained in the map user information is shown on the map expression data, to the terminal apparatus.