Hi Courtney,
What an AWESOME Christmas gift! As a mother of all sons, I can completely understand wondering about upgrading your room to stay in a pirate room; when my sons were younger, they would have loved them!
I think it may help you to look at different photos of the rooms to see if the decor would be something your son would enjoy. If you click
here then click on
Rooms, you can see two photos of the rooms.
But what may be even more helpful is to visit www.allearsnet.com and click on
Walt Disney World at the top. Once there, click on
Accommodations. You'll need to scan through the resorts to find
Caribbean Beach Resort and then click on
Photos - Text Links. Once there, you'll see a video of the Pirates Room which shows quite a bit of detail about the room (fyi, it is a wheelchair accessible room so there are some modifications). You can also explore many other photos of the resort if that helps.
And finally, www.disneycaribbeanbeach.com is another insightful website with plenty of information about the resort, including a pros/cons article about staying in the pirate rooms.
Please let us know if we can help again, and thank you for your question!
PS Have you heard about the Pirates League? If you click
here, you can read more about it in case you are interested in it.