Can't help you with your logistical Questions. But, I would reccomend that you not ride this route in the rainy season on a scooter. I've done my share of overlanding in Africa on a Classic Vespa, even in the Budapest to Bamako Rally, and can only urge you to do this trip. But the route you will be taking will be difficult enough under the best of conditions... I've not actually done the route you would be taking as I always have time constriants that would not allow me to ride this route on a scooter, but have allways wanted to. Please keep us updated...
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