Late last year we got both of my sons up on the wakeboard by sliding them off of the swim platform where I would sit and hold either their board or boot to help them balance. They really liked it so we tried again earlier this year but the water was too cold and when they fell in, both of them were done and would only ride in a tube.
We ended up buying them some EZ ski's which my 4yr old tried and actually liked and did well in. Over the last several outings my 4yr old and 3yr old boys both wanted to wakesurf with me. My 4yr old loved it.
This past weekend he decided he wanted to wakeboard but this time he wanted to get up behind the boat and not off of the swim deck. He wanted to do it by himself. He did great. We only got a couple videos of him riding but what's funny is that about half the time he got up regular and the other half he got up goofy.
You can see in the video around .49 he lets go with 1 hand and reaches for his shorts but falls. I asked him what he was doing and he said, 'I was trying to fix my shorts like you, daddy!'. The last clip in the video cracks me up. He said he was working on cutting back and forth.
http://www.youtube.com/watch?v=-PMeLP4xI8c