We have been studying a sightseeing support application using Bluetooth Low Energy (BLE) beacons and mobile phones since 2014 to support sightseeing in Nikko, one of Japan’s World Heritage sites. Travelers can receive information relating to their position by using this application. We tried to use some psychological effects to increase travelers’ satisfaction when they receive such information. Moreover, we tried to emphasize travel memories of the place (scenery, culture, food, etc.) to encourage them to revisit or inspire their friends to visit it. Our tests prove the usefulness of our sightseeing support application for enhancing the travel experience. However, we had not yet developed a function to provide information that met the travelers’ intentions or needs. Moreover, it is hazardous to use a smartphone during walking, especially in an unfamiliar place. If a traveler uses a smartphone during walking, they might miss the beautiful scenery, historic buildings, and exotic atmosphere. We tried to adapt our sightseeing support application for use with a wearable device (smartwatch) to avoid using a smartphone during walking and introduced a prospect theory to evaluate information according to personal interest and behavior. Our experiments proved that our application provided the most appropriate sightseeing information to travelers and prevented danger during walking.