Jost to Anegada is directly upwind in the most common wind conditions (ENE). There would have to be a lot of south to the wind, and then you'd be partly blanketed by Tortola. I personally wouldn't dream of it in a sailing cat.
I tried it once from Cane Garden Bay in a decent pointing monohull. Thought it would be a fun sail with the forecast 15 to 18 knots of wind. I was having a great time right up until the mutiny started!
