Oh, I sooo love your idea, OP, and will steal it to use on my trip with DS7 in mid-June! It's just the two of us as well on this trip and this will be an extra fun treat! It will be interesting to see how much ice cream one can eat before calling it quits!
My mom and I shared the chocolate chip cookie ice cream sundae at Gibson Girl for lunch one day and it was plenty after having a late breakfast. The cookies weren't that great though. I also vote for the soft serve at the cozy cone, my son loves that, and of course the Mickey bars!
I am very curious about the hand-dipped bars at Clarabelle's. I think we will definitely have to give those a try!
Have fun!!