My friend Kate is currently in a 500 km boat race called the Ngalawa Cup in the Indian Ocean - sailing a dugout canoe with outriggers and a single sail. (Ngalawa is the Swahili word for outrigger, and this is a traditional Tanzanian fishing vessel, although in my memory they were smaller, fitting only one person, and had a simpler outrigger. They were frequently partly or completely submerged, with the fisherman standing to his ankles in water.)
I would be in awe even if Kate weren't in her mid-50s. She's a fantastic sailor and has all sorts of training in knots, navigating, weather, etc, but this still seems impossible to me.
There are ten teams, and three people on her team, the Piratas Canadienses. Here are some links to info and updates: