I just planned out what I though we needed and went on a coast to coast tour (the Trans America). There were three of us together. It helped that we were all experienced with other outdoor activities including backpacking and some of us had done canoe camping and other self supported travel. Using an ACA route also helped.

That said it isn't rocket science. If you have some camping experience pack up some gear and head out on a ride. Doing some short shake down trips isn't a bad idea, but with some other experience it probably isn't a necessity.