wow lots of things lets start with some stories at the left http://www.horizonsunlimited.com/tstories/
That will get you a start then there the HU meeting in the 09 Canada West (date not set) the USA West in Colorado (date not set) that will get you face to face with people that have done it.
Now on the way down most seem to do it 3 to 6 months and try to hit it in the winter for the North, summer for them. Xmas seems to have get together.
As far as what see on the way there and back depends on what you want to see. but do take the Ushuaia cruise to Antarctica for $4,000 it will be money well spent.
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