We are going in December. My son will be 5 by then. He may barely fit in the current stroller we have for him by then. BUT, I will most likely lug it with us for the walk back to the hotel at night. However, I am also hoping to play with and see how this[/URL] would work for us. It's an option for your oldest while putting the youngest in a stroller. ALSO, if it's an option, buy a cheap umbrella stroller when you get there (I know that Disney World shops sell inexpensive umbrella strollers) and before you go home, give it to a family whom you think might need it.