D_O_J is being somewhat overly cautious.... if you had a support boat you'd be laughing.
You could definitely do it in a small yacht / dinghy, no major issues there, but I would say it would need to be something that won't fill with water to make it easier.
Laser II, B14, any form of
Catamaran, Tasar maybe.
Catamaran would be the best option; something fast - has been done as per above link from
Sydney to Tasmania.
It's a damn long way but not impossible!
It wouldn't have to be non-stop and there are definitely places to stop on the way for rest and shelter.
I would have attempted that trip in my youth but never really thought much about it. I had the yacht that was capable of it, the B14.
I was down off Wilsons prom over
Christmas, brilliant
weather, it certainly can be pucture perfect for sailing, but can get rough. That's why we have
weather forecasts.