Re: Sailing the Sydney to Hobart
There are some boats from the RSYS doing the Hobart race each year... So you can certainly ask the sailing secretary to give you the likely contenders and drop them a note or phone call.
The CYC has a crew list, I think it's actually on the net. As well as that just roll down there on a Saturday morning and see if you can get out with someone.
As for the experience you need, I would be doing the winter Harbour series to get you a better chance of getting on a boat for the Spring series, then the Summer.
Very few will take you unless you have raced the whole season with them.
So get cracking now! It's not too early to start working towards this years S-H
Notes on a Circumnavigation:
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