Our first trip was this past Sept. with our 4 y/o. We didn't keep it from her; we had her input from the get go on what to do and where to eat. We told her when we were going and showed her on the calendar and we counted down the days. She also earned Disney Dollars by doing simple tasks around the house and for good behavior.
As for the plane ride, how does he react to seeing a plane in the sky? My DD is absolutely facinated by seeing a plane or helicopter in the air. DW is terrified of flying, and told DD that she is afraid to fly. Me, although I was somewhat scared to fly, I had to be the tough dad and tell her I was not afraid. Since she knew that daddy wasn't afraid, she wasn't either. She absoluetly loved the plane ride, staring out the window the whole time and making me look with her. We did her homework (yes, preschoolers have homework now!) and had her chew gum. On the flight back, she slept pretty much the whole time, being it was a late flight, and I think she was just so exhausted from the trip.
If he might be afraid of flying , definately try to quell his fears well before you go. And as others have said, no papers needed, just his plane ticket.
Also, something else to keep in mind if he has allergies: Make sure you take his meds with you! The air on the plane had my daughter congested and sneezing as soon as we landed. The air in the room wasn't much better, and she was pretty clogged up the entire trip.
We booked the bounceback too for September and I'm already way too excited!!!:wave: