I'm envisioning a game app that teaches the user about the city. The user would increase their comfort level traveling through the city and visiting businesses and attractions.
The app would have an accurate map of the city with the ability to virtually travel through the city correctly using the roads and infrastructure. Travel options would include travel by car, bike, bus, and walking.
By car the user could virtually visit and drive around the city and just look around. The user could also pick a destination and practice getting there. The user would pick a destination such as a museum and practice choosing the roads to get where they are going. Once at their destination they would see parking options and other destinations nearby such as restaurants and gas stations.
The user could also start on foot at any spot and see how far/long you need to walk. You could also practice choosing the right bus and gain an understanding of how to get around.
The user could also choose bike paths and bike friendly parts of the city.
With the virtual tour in a game practice situation the user could play until they are comfortable heading into an unknown area. It would be like you had been there before the first time you set out.