1. Airfare not yet booked. Coming from the west, should we fly on 2/18? Stay a night in Orlando, wherever, or should we fly in on the 19th?
Do not fly in the day of the cruise. If you're coming in from LA, I don't think you'd be able to land in time anyway. Come in the day before, enjoy a day/night in Orlando or Port Canaveral, then come over to the ship at 11:30AM Saturday and enjoy the cruise!
2. What's the best way to get to the ship? I hear Disney offers a $49 per person airport pick up.
Believe it or not, it's cheaper to rent a car at the airport, use it for the night, then return it at Port Canaveral to the same car agency, but find one that has a shuttle to the ship from the drop-off location.
Or, you can stay at the Orlando Hyatt at the airport and hook up with
DCL Saturday morning at the airport. They will take you to the ship from there. No car needed, but it will cost $25 per person for DCL to take you to the ship.
3. What do I need to book NOW for shore / shipboard activities?
It's probably best to call DCL and ask about the excursions you're interested in. I booked the Coral World/Ocean Park & Island Drive excursion at St. Thomas, and I was left with the noon excursion. The 8AM was sold out. And this was a month ago!
4. What are the best parent/5-year old together activities?
Basically...almost any of them.
There's a little-known activity they run once a cruise called the Disney (or Mickey) 500. It's where they give you wheels, toothicks, car parts, a potato and a carrot, and you have to make a running car out of the potato and the carrot. Then you race it. It is an absolute blast! Look for it in the Navigators.