In this paper, we propose a method for automatic generation of music playlist that reflects a user's subjective preferences. The playlist is composed on top of a "Music Map" where hundreds of songs from various genres, which are subjectively characterized by the user, are topologically aligned. A playlist is generated by designing a travel path in the Music Map, visiting one song after another in a certain order. The topological nature of the Music Map ensures that the form of the travel path gives a certain character to the generated playlist. Thus, problem of generating a playlist that fulfills a given criterion can be transformed into a problem of finding an optimum path, similar to the Traveling Salesman Problem (TSP). In the experiments, we construct a Music Map containing 500 songs and automatically generate a playlist according to various criteria.