where to go this winter?

[Sooper8]

I can vouch for climate in Madeira.... Went a couple of winters ago. Unfortunately had torrential rain and some mud slips off the mountains.

Nuff said.

Yeah, probably should have made it a bit clearer. Been there 3 or 4 times in last 8 years or so and that freak rain was a one off. The locals had never seen anything like it.
Generally, the climate is great.
Very hilly though (and rocky)

[shane]

Ultimately whilst you might well have loved the Namib and Kalahari, surely they would have been more pleasant at the other end of the year when inland av max temps are in the low-mid 20s rather than the 30s you must have experienced, except right on the coast.

Naturally it would of been more pleasant to cycle at 20-25 degrees rather than the 35-45 I experienced, but it was very much a conscious choice to cycle that area at the height of summer for the full desert experience.

Your other points are also very valid, though I have a healthy disregard of what is the smart thing to do. I loved cycling through through the mud and dirt of Kenya the last couple of weeks at the height of the small rainy season. One of my worst experiences in Africa was the 140km of headwind through Kafue National park getting swarmed by hundreds of Tse-Tse flies, though seeing 3 cheetahs at 30m more than made up for the 10 hours of hell.