I started taking my son when he was just shy of 3. He hated strollers so we rarely used them, except maybe once or twice a trip late in the afternoon. I was a single mom so we just played it by ear and went with what he indicated he needed. Mind you, we always stayed in the monorail resorts since those were the only on site resorts at the time. We would go at his pace, if he needed to just sit on a bench and rest for 20 min. we sat. If he was getting too cranky for words, we would leave the park and either go back to the room or back to the pool. Usually back to the room and turn on cartoons, if he didn't fall asleep (or I didn't fall asleep) we would go to the pool for awhile just to give him some time away from all the people and noise. We always had park hoppers, always stayed on site and always just went with the flow. Lots of times he would fall asleep in my lap on the monorail or a bus and if that happened and we were on the monorail, we would loop it again, if a bus, I would just carry him back to the room or he would wake up and that would be enough nap for him. It really depends on the kid and the parents tolerance level.