My 5 year old doesn't require a stroller, but at a place like Disney, I would bring one anyway! I hated pushing a big bulky stroller, so as soon as possible I bought an umbrella stroller. However, I also hated that the typical ones were about 3 inches too short for me to push without slouching over. I found one at Babies R Us that is taller. I can't remember my brand, but the Jeep umbrellas are taller, too (if you need that). I never went the double stroller route, although I did check out the ones with the standing platform and also the little backwards bench...but they never looked like the right solution for us, either. I say push two. You are going to need dad (or somebody) to push the 5yo while you tend to the new baby, anyway. It will give you some more comfort to have them separate, IMO. Also, you may be lucky enough to find one that you could stash away underneath the big stroller if the 5yo wants to walk! My opinion...I've never been able to picture myself pushing a big ole double stroller! :)