I bought my 10 year old daughter a H14 this year. I hope she will be able to start sailing it next summer. Another dad in our fleet also bought a H14 at the same time and his 11-12yr old son had no trouble sailing it. Your son will be a teenager next summer and will want to go fast. The 14 can offer that with trapping.(attachment). We have 13-14yr old kids sailing H16's single handed in our fleet. If he can learn to sail and tack the 14 he will be able to sail about anything in the future.