A stormy, lee shore with few safe harbours most of the way. Quite the challenge. Are you talking about going down the west side to the Horn, or crossing "up" the Canal? Biiiig difference. Down in Chile, I don't know how you'd carry the fuel, water and supplies to get past Patagonia, but Vito Dumas Vito Dumas - Wikipedia, the free encyclopedia
The book "My Old Man and the Sea" might be instructive. I think that was a 25 footer. Don't bring a cat.