My kids have done fine on the boats once they were 2+. I had more trouble when they were 12-18 months.....they always wanted to be walking at that age and couldn't understand that they had to be held at least while the boat was moving. One of them also had a fit on one particular boat ride when she was 15 months old because she did not like having to wear the vest......screemed as if we were torturing her from OKW to Downtown Disney all because she didn't want the vest on. It wasn't hurting her in any way....just one of those toddler things. I felt terrible since there were others with us on that boat. I imagine they couldn't wait to get away from us! Even though 2 year olds have reputations for, well, being 2, they at least understand what you're saying, e.g., you can get up and walk when the boat stops. I worried given some of our earlier experiences but never had a problem with a 2+ year old. It's certainly a lot of effort to keep a hand on them at every minute, but the good part is that he'll probably really enjoy the ride, and it's fun to see the world through the eyes of a 2 year old.