Hey all! I know I'm a ways out but I'm a planner at heart and have already started thinking!

(we're not going until Thanksgiving for 10 days!!)
If the pixie dust is flying when I plan, I'll have breakfast ADRs at CRT. I'd like to do the castle cake mini and the slipper for my best friend and my other best friend's daughter. I thought I'd read at one time that they did pirate chests or pirate ships for the guys (it would be my two little boys who could possibly share one depending on the size). Do they still do something for the boys?
I'd also like to do a custom cake for either a Wishes cruise or lunch at the Grand Floridian. I love the white chocolate monorail and the Disney stamping (like on the fancier wedding cake styles). I also love the Christmasy flowers like pointsettias that I've seen on other cakes. I don't want anything too super fancy (my best friend and I would love it but I don't think the boys and kids will love it). I'm thinking buttercream icing on a white cake. Can I do that to get the nice stuff on the outside or will it need to be fondant? I don't have anything specific in mind - should I find something specific or will I have better luck leaving it up to them at the bakery to figure it out? It will be just a general "celebration" cake as it's my DS3's 4th bday 4 days before our trip, my bday 11 days after the trip, we "revealed" the trip as a birthday gift to my best friend and it's her and her son's first trip. I can't afford a cake for all of those different things so I think a general "celebration" cake of some kind is probably the best.
We've had custom cakes in the past and I haven't really been following along on process changes and things like that. I need to get up to speed before our trip. Will it be easier to get a cake for the Wishes cruise or at the GFC?? The best cake we ever had was at CR but we're not eating there (as of right now) on this trip.
Thank you all for sharing your amazing cakes and tips and tricks to get what we'd all like in our cakes!