Two things: 1.) Yes, Caleb is usually way too big for a stroller at 5 years of age. BUT, if you are trying to fit everything into one day at Magic Kingdom, you have to stay on the move and little legs get tired. Also, the crowds were crazy (summertime at Disneyworld = mayhem!!) so it was so nice for him to jump into the stroller after a ride and we had one less kiddo to worry about. And lastly, we could hook our backpack to the stroller and put all our water bottles in the basket and that was nice for all the adults!
2.) Caleb is wearing headphones in a lot of the pictures. This is not because he can't go a day without his favorite tunes. He has sensitive ears and doesn't like loud noises, so this helps him to be able to go on many rides that would be uncomfortable for him otherwise.