Best Stroller for Tall Preschooler

I would just use the strollers they have available at Disney. Why buy and lug something along when you can just use what they already have available at the park? I think they also have wagons too, which could be a good option if he's able to walk at least part of the time.
And keep in mind, STROLLERS ARE NOT ALLOWED IN LINE, which is where you will be spending a fair amount of time (you park the stroller outside the entrance to almost every ride/attraction.) Disneyland involves a fair amount of walking but it also involves a huge amount of standing and waiting.

The Disney strollers are really nice! They are comfortable for the kids and so easy to push. They also keep the kid well shaded.

I know you said he doesn't need a special needs stroller, but I think it would be a good idea to at least look. The reason being, very few kids still use a stroller past the age of 3. Since there aren't too many kids using them, there aren't too many parents looking to buy them. Since companies have no one to sell them to, they aren't making them. If you look into special needs strollers, at least you will find some tall enough for your son.

I agree with looking into a special needs stroller. Even if your son doesn't have special needs, chances are you won't find a stroller that will accommodate his size comfortably because most kids are out of strollers by that age... The easy to find/mass produced ones are made and marketed for babies and toddlers. Those made to accommodate older children are harder to find... Especially if you need the size to last a while.

Otherwise, maybe you can alter a some that are too short. Maybe get some plywood in the size you need, then use quilt batting to make a padded backrest and staple some fabric around it... Then attach one side of some Velcro to the existing back of the stroller, and the other side to your homemade backrest. Or, just get a small travel pillow and attach straps to it, then tie the straps to the sides of the stroller so that the tension holds it taunt enough to support his head.

There are 4 different places at Disneyworld to rent strollers, and you can check a few out to see if they are a type that would work for your son:

https://disneyworld.disney.go.com/guest-services/stroller...

Scroll down to see the other companies who rent strollers too.

I have a Chico Capri Umbrella that worked perfectly for my almost 5 year old in Disney World last February. It's not fancy, but lightweight, easy to fold and unfold, comfy enough for her to crash in, easy to push, has a soft plastic footrest, has a sun shade and pretty good storage underneath, even unzips to recline a tiny bit. They're not very expensive either!

I am a LONG time away from strollers, but you might want to peek at some 'special needs' catalogs...

They make some light weight 'umbrella strollers' for bigger kiddos!

best

I agree with the ladies who suggest getting a rental. Also, since he rather light, perhaps Daddy could carry him on his shoulders as needed? :-) That's always fun.

Rent Disney stroller. They are great. My 2 yo granddaughter is 35 inches. She is not really tall. I have a Britax which is fine for her. I am sure it will last for quite a while. Although I am thinking another year and she won't need it

We had a student at school that had a "scout" Convaid stroller.......

http://www.dejay.com.au/wheelchairs/strollers/convaid-cru...

I realize they are expensive, but if he has medical issues, you might get assistance buying one.

I don't know how well it folds up for travel, though.

Also, what about just renting a wheelchair? It might be much more comfortable for him.

When we went to Disney, our youngest was 4. We just rented a stroller inside the park when she got tired of walking. It was great, because we didn't have to haul our jogging stroller down there, and didn't have to worry about anyone walking off with it while we were waiting in line for rides! The strollers that Disney has for rent tend to fit good-sized kids. I saw a lot of kids who had to be 5 or 6 sitting in them, and they fit.

We used our citymini for our 3.5 year old, who is at least 40" and 40lbs when we went to London. We hadn't used it since he was about 2, but it was a godsend when traveling. It was really handy, especially in the airport when we had to make the gate, but couldn't afford to walk at his pace. While in London, he spent most of the time pushing the stroller, and we'd occassionally insist that he sit in it, i.e. through crowded train stations, when he was getting cranky and we were miles from the hotel.

Not sure what the rules etc are at disney, but if you can re-visit the city mini, it will certainly accommodate your child.

Best,
F. B.