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Self drive Cape Town to Namibia - help with itinerary

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We have decided on a last minute trip to Namibia, we will start in Cape Town and would like to drive up to Namibia and return to Capetown, we have 3 weeks for the trip but would if possible like to spend the last week in South Africa. Can anyone reccomend a good itinerary for this circuit.
We will leave on the 5th of October, what kind of weather can we expect?

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