seggie, let me give you a hint. The clue to pulling something like this off successfully - a STROLLER
I never leave home without one for the baby I do daycare for. She's 16 months old. It lets her feel like she's independent while in reality, I still have firm control
AND I have two hands free if I have to use them, as well as the use of the handles of the stroller to hang things from, the bottom of the stroller to stow things into, etc., etc.