Ok I have two teenagers, but I also have a five year old who likes to dart once in a while and gets tired easily, I do have an umbrella stroller but he is so tall, I am afraid if he falls asleep his feet will be stuck on the wheels? I still want to bring one for when he gets tired, any tips, anyone rent them? He is skinny but long legs. Also I have a hop skip jump diaper bag that I love, no he isnt in diapers anymore but its so convenient it is the duo, I just dont know if its too big, I used to hang it off the back, but occasionally if too full my stroller flips over, lol. Anyway any good bags out there? I like to keep a few ponchos, water bottles, face wipes, sunscreen, a water mister, and a change of clothing in there since I will have a small purse
. I for one see nothing wrong with the stroller for a five-year-old. My daughter will be five in a few weeks. She is my fifth child (out of six.) She weighs 31 pounds, and could not keep up with the rest of us if she had to. If I were heading to Disney World tomorrow, I would most definitely have a stroller for her.