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I have seen from other posts that it shouldnt be difficult. One should go first to Konso, then to Moyale and finally to Nairobi. We would be in 5, is it safe? I think that going from Addis via Dila rather than Konso is the more direct route. You can generally get your Kenya visa at the border but that will depend on your nationality.
When I did this in April , it cost 99 birr on the bus from Addis to Moyale - you overnight in Dila, so will need to pay for some accommodation there. Most of the truck transport leaves Kenyan Moyale about 9AM, so you will need to spend a night near the border - I don't know what time the border opens, but if you have the choice then I would spend the night in Ethiopian Moyale as the Kenyan side is pretty grotty.
Try to get to Kenyan Moyale for 8AM or so, to have the best chance of getting a decent seat on a truck. There is a bus that runs but it only goes if it's full, which seems to happen about twice per month. Hitching is another option, but you'd be lucky to get anything that can take your whole group. The road from Isiolo onwards is tarmac and there are scheduled buses to Nairobi from there KSh As for safety, you're probably more at risk from a traffic accident than anything else. The stretch between Moyale and Marsabit used to have sporadic bandit trouble but I don't know if that's still the case.
Bear in mind that this information is now 2 years old, but I'd be surprised if the situation other than perhaps prices has changed much. Thanks for the infos! If everyone has other tips to give me, feel free to do it!
Did you manage to do the trip if not i might update you on the Road past Isiolo to Archers post is ok and the road up north is being improved we hope this can be done faster. Transport costs have gone up and you wont get something less than a thousand. On transport, you will get a lot of taxis, mainly toyota probos and g-touring operating on this route, You can take this straight from Moyale to Nairobi or get to Isioolo and take a bus or minibus matatu to Nairobi depending on your budget.