I am thinking about taking my 2 1/2 y/o grandson to WDW for some GM-GS alone time. My D-I-L is not a Disney fan and has no intention of ever taking him. Both she and my son have said they have no problem with me taking him anytime I want though, so I am thinking of taking him on my upcoming Nov/Dec trip. He won't be quite 3 y/o. The only thing I'd take on the plane would be a backpack with stuff we might need on the plane, so I'd have both hands free to deal with him. I'd be renting a stroller from one of the offsite places down there. My only concern is getting him through airport security by myself. He has never flown. He is an easy going kid that's very easy to take care of, but can be timid when it comes to new situations. He's not going to like me putting him down, then having to wait, while I walk through security by myself, before he can come through. If you are by yourself, how do you get yourself and a toddler through the scanners? Also if you were by yourself, would you mess with dealing with a carseat or just let him sit in the plane seat? We'd be using Disney transportation, so would not need a carseat in Orlando.
The only thing I was really concerned about was getting him through airport security by myself and if we needed his car seat on the plane. Oh, and convincing him to take his shoes off to walk through security.
and also a stuffed Shamu whale. The morning I was packing to come home, I was having to squish her rabbit and Shamu into her carry on. I had the rabbit face down, pushing him in. She started complaining I was going to hurt her rabbit. I told her either I squeezed him in, or he got left in San Antonio. She ran over, started stuffing him in with both hands, saying "hold your breath, hold your breath, you gotta fit".
). Since then she obviously gets her own seat and I just buckle her in. Having to keep up with a young child, stroller, carry on stuff, etc by myself is enough to deal with without having to manage a carseat, too. In the past I have considered renting a CARES harness, which is made for a plane (and you can rent on eBay), but just never did.