I did it a few years ago on a big aluminium schooner. We ran the southern
route, Hobart, south of NZ with a quick stop at
Auckland and Campbell Islands. Then on to Puerto Montt. It was early October that we left.
Weather was pretty good, I suppose we had our share of rough westerlies, but nothing nasty. What surprised me most was the variability of the
wind, it certianly wasn't nice steady westerlies. So we had lots of sailhandling and regularly went from drifting with light air sails to heavily reefed over a few days cycle.
We were down around the 50's for much of the trip with occasional snow. So gloves were essential. And a decent
dodger to prevent to much
water below would be real handy.
There is some stuff on my blog about cold weather
gear.
And a video here
https://youtu.be/CJMIBbt2svo
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