Desmond's "Race Around the World" has to be either

[happjack]

of the around the world sailing races either the one with Americas Cup style boats with a large crew or most likely the solo around the world race in a small boat. I think he ended up crashing on the island and took up residence in the abandoned bunker, there is no way he has been there since the 1970's when the thing was built. I don't know of any two man around the world sailing races but they could have it where it was a two man race they crashed on the island and his partner Ethan went nuts and Desmond took to hiding in the bunker and fearing "the sickness" that he could have read about in some of the logs they found from either the French from 16 years ago or the bunker builders from the 70's.

[clayseason1]

or

south pole race around the world (http://www.cmdl.noaa.gov/gallery/south_pole_summer/Worldrace)

[Max Power 79]

Yeah, I think Desmond crashed on the island in a way like Danielle. However, he did seem to need the Medicine, so either he brought it there or maybe the Medicine is an antedote to whatever disease was on the island.

What if "Race Around The World" meant a space ship and he crashed onto the island?

[LostInWilderness]

Or maybe it's like "Around the World in 80 Days."