Microsoft AutoRoute 2007 is a great software for planning a road trip. You can find any address and landmark in the map. There is a world map, where you can zoom in. All the road and rail routes of the United States is marked in it. There is a Euro version of AutoRoute too where you will get the whole of Europe. Anyway it is not available for Asia, Africa or other Ameriacan Places.
It has the data for the road map, and all the landmarks and hotels, motels and restraurants, with their telephone numbers!
There is a route planner where you can add the place by browsing on the map. For example, specify one place as the start and add as many places you need to visit. Add / specify another place as the stop. Now click "Get Directions". It will automatically generate a directions chart / schedule. You can also specify the start time and it will schedule everything and calculate the time needed. You may also specify the time needed for a particular place.
Instructions like "Turn left", etc are automatically generated. A summary pane shows the total time that would take and the cost in any currency !
You will also get the specific latitude and longitude coordinates for any place just like a GPS.