Buying a Sailboat does it make sense

As to dinghies: If you can't very easily sail a laser or sunfish (etc) easily across a river and around pilings and basically be able to put it anywhere you want, you shouldn't sail a large boat. Dinghies teach you great sail handling. Sail backwards. Sail in crowds.

Small boats first for skills. Bigger boat skills are different but the sail theory is the same.

 

Dan,
This is how people die on the water. Someone mentioned sailing classes, I would say you need a cruising course to discover if you really want this type of life. Next I would say you are years away from handling a 60 foot vessel. 30 feet is a nice size to start with in a charter. You'll be able to get in PLENTY of trouble with this size and learn a great deal at the same time.
Best of luck, but please go slowly with much knowledge.

 

Learn basics on a sabot and go from there. You are in WAY over your head with a '60 footer.

 

All great advice, thank you.
I did the dinghy-thing, and a course on some 4.7 mtr boat in the south of France many moons ago, funny enough came accross the diploma I received the other day. That's pretty much meaningless in the current scenario.
Fortunately there's a good marina closeby, with lots of crew-less yachts and the waters of False Bay and around the Cape of Good Hope on my doorstep, which should provide ample opportunity to make miles on different boats. I guess that's where I'll start.

Best,

Jack.