Update on this situation: After speaking with a bunch of people in the know, I concluded that I most likely wouldn’t have any problem getting into Senegal with a one-way ticket. But I also concluded that in the very unlikely scenario that I did have a problem, there was a distinct possibility I could be barred from my flight and lose the 40,000 frequent flier miles I spent on the ticket.
Rather than taking that risk, it seemed like a better deal to get an onward ticket for a random destination and arbitrary date, and to write off the change fee that I’ll eventually pay – when I figure out where and when I’m actually going next – as the cost of entering Senegal.
United’s rules for mileage tickets are pretty straightforward, and pretty reasonable. It costs between $75 and $200 to change the ticket or refund the miles into your account. So I booked a one-way ticket out of Dakar on May 12, the last day I can stay in Senegal without a visa (which BTW you can only apply for once in-country).
The destination? Casablanca by way of Lisbon, because the first twelve cities I chose didn’t work out for various reasons related to my inability to make anything easy for myself. At first plugging in Dakar – Nairobi, Dakar – Kigali, Dakar – Accra, Dakar – Cape Town felt really worldly and exciting, but as one destination after another proved logistically impossible I became increasingly frustrated and worried. I know this is just a placeholder ticket but booking it has shown me that traveling around Africa on airline miles is not going to be easy, and traveling around Africa with paid tickets is not going to be as cheap as one (who is naive) might have thought.
Well, I’ll figure it out eventually. There’s a lot of time between now and May 12.