Welcome Simone. It sounds like you have a great holiday planned! What day is your cruise? There are a few of us cruising on the 21st. I'm no expert on booking WDW and have many of the same questions you do. Just a thought though, if you are hoping for the free dining plan, be careful about booking tickets separate from accommodation. I could be wrong, but I think free dining can only be added to a package i.e accommodation and tickets booked together.