For my granddaughter, it was 20 kids and two Cast Members on the boat (not including the driver). My daughter-in-law was a nervous wreck with everything. This was my Christmas present so I had made all the arrangements and plans.
All I can tell you is not to worry about a darn thing. Get there about 9:00 when the restristration first begins. Your little pirate will then need to pick out a life jacket and this will definitely be checked by a Cast Member for proper fit. By getting there early, you can get great pictures with the Castle in the background before any other pirates show up.
Around 9:25, all the pirates will be gathered together and paired up. They all will have pirate bandannas on with their names. They will board the ship (a party boat with a Jolly Roger on the back end) in pairs. They will be with that buddy for the entire time. I really doubt anyone can wander off on his own.
BTW - you (or the adult in which the reservation was made) will need both your receipt AND the beeper to get your child back. Once the pirate ship docks, the Cast Members will go down the line of parents and will not let a child off without having both things. They won't let a child off without a parent either.
After going through a half hour of worrying, my daughter-in-law, having seen the boarding process, actually relaxed and had a great next two hours.