Hi Joseph. Not sure where you guys are at the moment but maybe this is of some help.
Following arecent visit I have some news on the condition of both routes from 12th January. I was told that the salt flats were wet and impassable and took a jeep tour. It soon became clear that it would have been possible to ride on the salt flats from Uyuni out to Fish Island and back. The southern part of the flats were under a few cms of water and I would not have wished to ride across. The jeep tour then continued south through San Juan and down to Laguna Colorada, Laguna verde and back to Uyuni. There was heavy rain after we left the salt flats and the roads became quagmires. I decided that I would not ride along route 5 to the border at Ollague. Simply too much mud. However, the alternatives (routes south to Laguna Verde and the border near San Pedro De Atacama) were looking very bad too.
Ultimately I chose a route from Uyuni to San Cristobal to Alota to Ollague. This route (from Alota to Ollague) was not marked on my map. The surface was generally hard (with very little sand) all the way to the border. It is gradually being improved though and shopyuld in future be a good road. However, just outside Uyuni you need to cross 2 rivers. They are currently building the bridges. The first one (Rio Colorado) had to be crossed by truck. The second was just over boot height. Lovely. If anyone is facing a choice between routes during the wet season I would recommend this one. But it is not nearly as scenic.
At Ollague (150 miles from Uyuni), I could not even find the place to exit Bolivia. Rolled into Chilean customs and they promptly confiscated my sheepskin seat cover. If you have one stash it in your bag!
The road to Calama was terrible. Corrugations and loose sand but probably still better than the route through southern Bolivia. The road was unpaved for the first 120kms then badly paved for the last 80 kms to Calama.
PS Last fuel is at Alota - available at the general store. Then it is 280kms to Calama. There is no fuel or money changing at the border.
Hope this gives you some clues.
Matt
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