Call me a ****, but after reading the posts on this thread I have decided not to take the young'un on this ride. We won't have time for enough preliminary training. I don't want to push him. One day is going to be 70 miles and he has never ridden anything close to that amount.
Instead we will be doing our own unsupported tour. That way if he gets tired or loses interest we can stop. It will give us more flexiblity. This just seems like a more prudent way to go. If it goes well then I can sign him up for an organized tour.
Thanks for all the help.