Is this the most circuitous route on Google Maps?
As you can see, Google Maps knows all about the Madre De Dios River ferry dock in Puerto Maldonado, Peru, but it hasn’t figured out that means you can actually cross the river there. So if you ask it for driving directions from Route 26 in Puerto Maldonado, to the ferry dock on the other side of the river (a distance of maybe quarter of a mile), it tells you to take a 5,022 mile road trip through Brazil, Argentina and Chile and back into Peru, carefully skirting Bolivia and Paraguay on the way. (Incidentally, I doubt if anyone could drive this in under 5 days, as Google seems to think.)
Another extreme example is the route from Moyale, Kenya to Moyale, Ethiopia. Instead of telling you to use the border crossing there, Google Maps suggests taking a 3,603 mile journey via the A43. Can anyone beat these and find an even more circuitous example?