The number of foreigners who visit Japan is increasing lately, however most of the services or products for foreigners are designed based on their superficial understanding and do not meet their true needs. This research’s goal is to propose place oriented Internet radio called “Re:Radio”, as a new media to help foreigners understand Japan at a deeper level, by providing individually customised contents. Specifically, the dialogue between a guest and personality is used as main contents. Listening to the contents at the place induces listener’s self-reflection, which helps further understanding of the place. This paper introduces the concept and implementation, and the experimental results conducted in Tokyo.