mabbott said...
If you are not interested in racing and not that flexible ie trying to get under the boom, then a simple boat for cruising with a couple of people would be the Hartley TS16, it is 16ft in length as the name indicates. Personally I've never owned one. Could be worth considering. Not that expensive.
A helpful link is http://home.iprimus.com.au/youngenr/ts16/index.htm. Has some pictures and general info.
Cheers Mark
I second this suggestion! TS16s are great fun to sail and there's a big racing class for them. Proabaly best for only 2 people, but for 3 you could go for a TS18 or even TS21 (although that might be tight in the garage). I've never seen one but might accomodate 3 people a bit better.
I also really like the Cole23 or a RL24 for cruising yachts, but again you would need a big garage!

Before he forks out any cash though it might pay to take him down to your local sailing club and get him to crew for someone else, firstly to get experience and secondly to make sure he enjoys it. Owning your own boat can be quite stressfull at times.