We have also taken two kids as babies and did not stop for nap breaks and just let them sleep in a carrier or stroller.
yeah we found this to be a bigger issue than naps as well. Our infants/toddlers really wanted to move and that is hard in the parks when they would be apt to get trampled. 8 or more hours in a stroller or sling is a lot of time trapped in one place. Some of the play areas at WDW can be reasonably quiet even on crowded days and are good spots to let a little one crawl or toddle a bit.
My son was a car seat/stroller sleeper so he would take naps in his stroller. We would grab a snack, DH would hit a big ride we couldn't go on, find some shade, etc while he napped. We found that for us, it was best if we hit the park early, kept on a regular eating schedule like we had at home, and then let him nap when he wanted and for how long he wanted in the stroller and then headed back to the resort after dinner for a regular bedtime. In the years since, we have kept the pattern the same. He is 3 1/2 now and doesn't nap any longer, except the occasional cat nap in the car. We still hit the parks early, if he dozes off we let him, and then head back after dinner. We might only hit a night show once or twice. I think the best advice is to be flexible and it is normal for the schedules to go right out the window. I want to add, he went right back to a regular schedule when we returned home. Have a magical time!!!!
In order to try to get a snooze in, we would take a path less with less foot traffic and put the hood of the stroller up and recline him back. We also got a portable fan to clip on his stroller so he was nice and cool. And we would walk for longer to try and get him to sleep. Most of the time though, he would just doze off with out us really noticing...like in line at Peter Pan the first time we took him!!! It will be interesting what happens when he is 4 for our next trip. I don't think there will be any snoozes. our first trip with young grandkids we found going back to resort a big big mistake. 16 month old fell asleep on way back and screamed and I mean screamed could hear at other end of hall and then fell asleep during dinner. worse day ever in park. with your son I would see what happens a few times if you take a car ride of about 15 minutes and try to move him to bed close to time you have trip planned. remember that from park you have to get back to your resort then walk to your room plus we are never near the front of park at nap time. it is not as simple as going to his room and putting him down. my grandkids would just lay back in stroller and relax as we went and most were not normal stroller nappers
just remember that short walk from front of park can take almost 30 minutes from far side of park counting time to front gate
