We did it in August for the first time and we all had a ball! DGD (age 1) was in a stroller and we didn't have any problems at all. In fact, we were the only family on the tour so we finished about 30 minutes early.
The CM will make you feel comfortable with all the silliness. Our 16 yr DD was not too sure about the whole thing when the CM called her by name while we were in TomorrowLand. Sensing that she might be slightly embarrased, she quickly said, "Now all those cute boys know your name. They will be looking all over the park for the rest of the trip, calling out ______!" Just about that time, one of the guys winked at her and she was thrilled. The CM knew just how to get us all involved and out of our comfort zone with public silliness.
Let us know how you like it!