Remembering back to when I when from Cubs to Boy Scouts as a kid, I remember feeling like it was all starting over and not as if I was 'transitioning'.  It was a whole new world with new older boys that I didn't know.  Fortunately, 3 other boys when from the same Cub Pack to Troop at the same time which made it a little easier.  We all eventually bonded but for a while it was basically us 4 boys and the rest of the Troop.

One thing that I am going to be working with our Pack on next year (and this) is getting the Boy Scout Troop that is common with our Chartered Org to start to be more active with us or us more active with them.  We don't currently have any den chiefs and I would like to at least try to see what can be done there. 

On another note, Cub Scouts for my son is much different that what I did as a Cub.  I remember the crafts and the den mother and not really any outdoor skils, etc.  My son has already experienced way more camping and outdoor skills than I had when I transitioned into Boy Scouts.  I believe that will make it easier as well to already be familiar with that aspect of scouting which is a large part of the Boy Scout program.