I haven't yet taken a child to Disney world. We have one child and DD will be 2 1/2 when we go in the fall of 2014 (happy dance). Hovever, hubby just got hired as an airline pilot so packing for kids is something that I could have gotten a college degree in by now it feels like.
One thing that I've put together for my daughter, as far as sleeping arrangements go, is a "bed in a bag". If you are flying to DW, this can be a lifesaver on getting through airports with less headache. I got a pack and play for her expressly for travel (about $45), and I have a pack and play matress that I bought off of
Amazon, because the pad that comes with the pack and play is only an inch thick and hard as a rock. I had no idea how I would be able to transport the matress without losing valuable luggage space. So I went to a discount store (Ross) and found a $50 extra large rolling duffel that had a lot of external pockets. Lo and behold, when I collapsed the pack n play (Graco Brand), wrapped the extra matress around it, and shoved it all into the duffel bag, IT ACTUALLY FIT! I also put the fitted sheet and an additional padded matress cover over the extra matress before putting it in the duffel. In the external pockets I was able to put a large fleece blanket, a travel cloud b sheep soundmaker, a lovey, binkis, and still have lots of room left for miscellaneous items. This way DD has something familiar to sleep in when we travel, which I know is comfortable for her, and stays clean and protected while travelling, and I dont' have to go to the trouble of renting one (and they are not guaranteed to be available). It also cuts down on that ick factor of using a multi used sleeping place for my baby. Hope that helps!
For me personally, planning for packing is the most crucial thing. I don't enjoy the idea of touring plans, etc b/c part of the fun for our family is seeing what we feel like doing for that day and going with it. However, I take the opposite approach when packing. I am not someone who does well when I can't get something I need easily.
There are a lot of packing checklists on several planning forums across the web that are tailor made for Disney. You can just go down a checklist, which will help you to think of things that you may not have considered you might need. I would never have thought of bringing a rain poncho for example but after reading forums it seems like such a little thing that can go a long way.
Another great idea that I'd heard (since orlando is notorious for having a small unpredictable rain showers) is to bring a collapseable stroller rain cover and use it before going to get on rides. One traveller mentioned using one just in case and when they came back from the ride, theirs was the only stroller that was dry. Keeps the diaper bag and contents beneath dry too.
Other than that I would say read your kiddo. Dont' push them to tackle the whole "world" in a day. If they want to run around chasing a butterfly (something they could do at home for free) let em. Just remember that you can enjoy the fact that you're in the most magical place on earth the whole time, enough for both of you, and don't pressure yourself. It makes the whole trip so much more enjoyable! Hope you have a blast!
