This study emerged from the question of how mobile handsets can change the nature of cultural and historical tourist experiences in ubiquitous city environments. The paper describes the development of a new and entertaining type of mobile tour guide system that positions the mobile handset as a key delivery system for site-specific cultural and historical information. The central objective of the project was to organize a cultural and historical walking tour around the mobile handset and its unique advantages (i.e. portability, multi-media capacity, access to wireless internet, and location-aware potential) and then integrate this tour with a historical story and role-playing game that would deepen the mobile user’s interest in the sites being visited, and enhance his or her overall experience of the area. After prototyping and user testing, new strategies for developing mobile information service with entertainment elements to deliver cultural historical content of the location were considered.