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jswinnyc said..
I will visit for the first time next week (my daughter there for work, I will tag along). I am an old long boarder, very experienced, will be in Sydney. I welcome and appreciate any recommendations for where to rent and sail, where to stay, etc.. Thank you. Note, I also wing (and kite, witefoil, etc.), so if there are better bets in Sydney, would love to know.
The longboarding centre in Sydney is Dobroyd Aquatic Club, which has twilight and weekend racing. It's located on a skinny arm of upper Sydney Harbour, a few milestones west of the CBD. If you contact them through the website they may be able to get you on one of the training boards and you can get out for a social race and pizza afterwards.
Balmoral Sailing Club apparently has a club Windsurfer LT for new sailors that you could possible get. Balmoral is much closer to Sydney Heads and can offer better sailing on a good day than Dobroyd, but there's lots of boat traffic on the weekends.