Hi elsawasajedi -
I've been on the Fantasy a few times... have actually done this itinerary. But have not experienced everything you mention above.
Below are some thoughts.
1) Have not done the "dessert experience".... wonder if that's somewhat new?? We have done "Remy's Champagne Brunch" and will say that is awesome. An expensive... ($75 pp I think??) but great experience.
2) Remy's is really a special experience. If you decide to book dinner, expect to spend 2-3 hrs there. You should be able to find menus online. The cheese cart rolled out towards the end of the event was the highlight for DW and I. But it's really special. Highly recommend. I believe it's $100+ pp to book. But worth it in my opinion. Have never done massages and never traveled with children so do not know much about the Oceaneer's club. Families we met on sailings usually make sure the kids have dinner and are scheduled for the Oceaneer's Club or other supervised kids activities during your dinner experience.
3) Formal night and pirate night are not on the same night. At least they never have done it that way on my previous cruises.
4) DW and I have never traveled with children and never attempted to "find a spot" near the pools. I do know getting a spot can be competitive. You will see people getting up early and leaving their stuff in an area in an attempt to reserve their spot. I believe that is discouraged but I don't think they enforce it.
5) Watch the character greeting schedules on the "Daily Navigator" and try to line up early if you can. The Daily Navigator is a paper guide made available each day (night before) at the guest services desk. You can also download the app... "
Disney Cruise" much more convenient than running down to the desk for the paper copy.
6) So the wife and I (DW) are not wine aficionados but do enjoy adult beverages onboard. I'm a beer snob, she likes mixed drinks. They do have premium beers.. Belgian Quads, Trappists, Stouts... So I'm confident they carry high end wine options at the restaurants/pubs. Be prepared to pay the Disney premium. The wine package I believe is set up for folks who like to have a nice wine with their dinners. But the wines in this package is definitely NOT representative of everything available. They have Cognac that sells for $300 an ounce for the folks who have a high end taste.
7) Depends on the time of day and where the ship is at. If we're in port and you're not going ashore, that's generally when it will be least crowded. But the line is usually 20-30 minute wait in my experience.
8) The water at Castaway Cay might be a little cool in December. But nothing that you cannot quickly get used to. Water will be fine down in the Virgin Islands.
9) Yep... we like starboard but you need to book early. Everyone else likes starboard too!! View of Castaway Cay when we're there and fireworks from your balcony are usually the top reasons. Fireworks are always shot off the starboard side on pirate night.
10) Deck 10 is right below the pool deck so you would hear more of the noise from kids running above.