Hi Robyn!
This is a tough one! The pirate rooms at Caribbean Beach are absolutely amazing - you won't find cooler rooms anywhere on property! However, they are a long haul from the food court and shopping area. While the location is not prime, there are internal buses that will bring you from Trinidad South (where the pirate rooms are) to anywhere in the Caribbean Beach Resort. The food court is average and I don't really care for their table restaraunt, Shutters.
On the other hand, Port Orleans Riverside is my favorite moderate resort! There is so much to see and do here that I could easily spend my entire vacation just hanging out and exploring. I won't lie, the rooms are nice, but not exciting. The Caribbean Beach rooms win that category hands down! However, the grounds are beautifully landscaped, the Sassagoula River is gorgeous and you are just minutes away from Downtown Disney. My kids love running through the paths and swimming in the old swimmin' hole. Everything is so relaxed and the cast members are so warm and friendly. Last but not least, we love the food court AND Boatwrights Dining Hall. My family always tends to head back "home" to this resort!
I highly suggest checking out the room photos and reviews on
www.AllEars.net. This site has pictures of absolutely everything - from the food court to the detail on bedspreads! Have fun planning and have a fabulous vacation!
Much pixie dust,
Jackie S.