G'day Matt,
Welcome aboard.
I'm not Sydney based, but a friend of mine told me that she got into sailing through a system that they have at the CYCA (Cruising Yacht Club of Australia) in Rushcutters Bay. Apparently you can sign up for twilight
racing where the club provides the yacht and an experienced
skipper and then "newbies" make up the crew and "learn the ropes".
Also, if you are serious about
purchasing yourself a yacht, your best friends are going to be
a) The Yacht Hub
Boats for Sale New & Used Yachts @ The Yacht Hub
b) Boatpoint
Used Boats - New Boats - Search New & Used Boats For Sale - BoatPoint Australia
These are easily the best web sites for searching for
boats in
Australia. Even if you are not yet at the stage where you are going to
purchase, it is well worth spending an hour or two per week looking through the
boat listings that are in your price/size range... it is, in my opinion, important to get a feel for the market... i.e. get to realise what the going
price is for a give size / age / type of boat. You will also find that looking at a few thousand
boats will help you to refine what it is that you are realistically looking for & able to afford.
Other than that, wlecome aboard, and get out on the water!
Cheers