In Orlando, $300 wouldn't last long for food, even if you do fast food places. My hubby had to go there for a conference a few years back. We stayed at the Contemporary Hotel. I couldn't find a sandwich less than $8 and that was tuna salad.
I am so excited for you! RCCL is a great cruise line and the Freedom is a great ship! I am going to bet that you will be booking another cruise before you leave the Freedom
Please let us know how it goes when you return. You'll be sailing right after us. I'll be back to work and you'll be on board