This is going to be one meticulously over-planned route. Ray and I started off with Google Maps, then clicked to "avoid highways" to get an idea. Then we set up a custom Google map [see sidebar] and collaborated online to set points for stops along scenic places and tried to pace it for a quick break every two hours or so. Now we're in the step where we find places to eat, sleep, and visit along the way. We're using a site called TripAdvisor that lets you pull data from people that have been to those places and made recommendations. Then we're going to use Google Earth to view crime stats for the areas, etc. before we settle on a hotel. Lastly we'll program the points into our TomTom One 3rd Edition GPS units as a route, and we'll use them on the bikes to ensure we don't get lost. Both of our cell phones are location-aware as well and will map to within five blocks or so by triangulating from the cell towers.
We should at least know where we are and where we're going. That's a solid step.