Our five year old has been out of her stroller since a little over the age of 2. We live in NYC and she has grown up walking all over the city and never complains, however, I KNOW that WDW is a lot more walking at one time and I just felt more comfortable having the stroller. We bought a cheap stroller with us -- we paid $11 at Target and figured if we had to throw it out after the trip, it was still well worth the $11! A lot of the time she ran around after her sisters and we used the stroller for packages. But there were plenty of times that she would just happily collapse into the stroller and got 'pushed around'. We flew down on Jet Blue and they LOVED the TV's!!! I will suggest EarPlanes to use for those sensitive little ears on the descent though. All 3 of my dd's refused to use them on our way TO Florida, and all 3 suffered miserably with ear pain upon arrival in FL. Thankfully it only lasted a few hours. Coming home they insisted I put them in and we had NO complaints of ear pain!! LOVE them!!! We also took along modeling clay, favorite stories, juice boxes (supposed to ease the pain as well), guide books for the older girls and I put together a Fun Folder for all three girls as well. These had some pages to color, some fun trivia, maps to the park, places to write how they feel about the upcoming trip, places to write addresses of those they want to send post cards to back home, things they want to see while there, and lots more. Our last trip was a surprise for our girls and I packed things for them that *I* thought they would like and I overdid it! LOL They didnt even use half the things I took, but better safe than sorry is my motto!