Hello Jaclyn!
Have you booked your resort yet? The Caribbean Beach resort has recently remodeled some of its rooms to a pirate theme. The beds are pirate ships and the carpet looks like wooden planks. The entire room is totally pirate themed. The main pool has also gone under a transformation and includes a children's play area with a pirate ship. You can see pictures of these rooms by following this link and clicking on "Rooms".
http://disneyworld.disney.go.com/resorts/caribbean-beach-resort/
In the Magic Kingdom, a new experience is about to open called The Pirates League. Here, your son can be transformed into a pirate before your eyes! The experience includes getting a new pirate name and signing a pirate oath. You can get more information by following this link:
http://disneyworld.disney.go.com/tours-and-experiences/pirates-league/ You can book this 90 days in advance by calling 407-WDW-CREW (407-939-2739).
After his makeover, take a ride through Pirates of the Caribbean. Occasionally, Captain Hook is available for meet and greets near the Pirate of the Caribbean ride. Check a park times guide when you arrive to see if and when he will be out and about.
Finally, there is a Pirate & Pals Fireworks Cruise available. This cruise departs from the Contemporary Resort and goes into the Seven Seas Lagoon where you can view Wishes. Before leaving on your voyage you will have the chance to meet Mr. Smee and Captain Hook. While they don't accompany you on the cruise, you will have a pirate host who will keep you entertained with stories and songs. This experience can also be booked 90 days in advance by calling 407-WDW-PLAY (407-939-7529).
I hope this gives you sone fun ideas for your little pirate!