Now I've read everyone's posts, I feel like I just have to document my own opinion.
I windsurfed on and off for about 10 years, usually on vacations, having never lived near a decent body of water. I found windsurfing to be pretty slow to learn. Things like the water start and the last move I learnt, the carve gybe, each took weeks of practice to learn. It was satisfying learning these moves, but it took a long time.
This summer, I tried kiteboarding for the first time, and the learning curve was much, much steeper. It seemed that every new thing I tried could be learnt within one to two days of trying. I was jumping at the end of my two week stint.
I live near a lake that gets moderate, but not strong, winds. Nearly everyone here who used to windsurf has made the switch and I'm planning to do the same. To my mind, kiteboarding has the following advantages:
- it is quicker to learn (this would be less important if I lived on the coast, say, but the days I get to do wind sports tend to be few and far between - I simply don't feel like I will have time to reach the level I want to in windsurfing)
- the equipment is more compact (I live in a small apartment, so that's pretty important)
- in my experience, it is more fun in moderate winds. I'm sure I could windsurf and plane in these winds, but I was never really a fan of big sails
- finally, I know some people have said they didn't like the 'light on the water' feeling, but I did. It is different from the feel of windsurfing for sure, but personally I liked it. I think the feel of the board is also very familiar to me from all the snowboarding that I do during the winters.
I do think that I will miss the satisfaction that comes from cracking new windsurfing technique after weeks of trying, and from what I have seen so far I also prefer the windsurfing community, but at this stage I am going to go with the kiteboarding... I simply think that at this stage in my life it will result in me having more fun.