Yo Ho, Yo Ho Melissa!
Thanks for visiting the Disney Parks Moms Panel. One of my family's favorite attractions at any Disney Destination is
Pirates of the Caribbean at Disneyland Park. It embodies so much of the spirit of Walt Disney Imagineering with creative storytelling, Audio-Animatronics, and classic music. It really is one of the most quintessential Disney attractions.
As you said, this attraction does not have a height requirement which means you can take the littlest swashbucklers on with you. We started taking my son as an infant and throughout his first three years of life. It still remains one of his absolute favorite attractions. While every child is different, I cannot say for sure how your son will react, but it may help to give him a little warning right before you know you will be dipping while you are on the attraction. I usually say something like "OK, here comes the fun part, hold on tight! Weeee!" You can also let him know that it is going to be dark and there may be loud noises. I tried using my own narrative to help my son understand what was going on, pointing to things we saw while on our boat. He loves spotting some of the animals like chickens, piggies, and cats to name a few.
We also listen to the famous song "Yo Ho (A Pirate's Life for Me)", as well as other Disneyland attraction songs, before our trips to familiarize him with what's to come. These can be found on the Disneyland Resort Official Album which you can purchase on iTunes. Another classic attraction that I use the same approach to is
Haunted Mansion, and coincidentally this is one of his top picks as well.
I hope you and your little buccaneer have an amazing time on your adventures at the Disneyland Resort.
-Jennifer