The only sure way to know when it is time to leave is when you find your wallet empty and your galley stocked. This is my present condition.
As I head north to the tip of Borneo I will look to the wind: If it is blowing an Easterly, I will head west 'about. If it is blowing a Westerly, I will head east 'about.
Either way, I will eventually wind up at the bottom of Borneo and will pass through Indonesia to the open sea, at last catch a trade wind, my first in longer than I can remember, and I will sail for the Chagos Archepelago, which I had to pay an Outrageous fee to enter. But it is supposed to be fine and it is literally in my way, directly on route to my landfall in the Seychelles. I'd have to go around it. So I'm stopping, and paying, and diving at will. Untill I run out of water, food, or gasoline for the dinghy.
My supplies are substantial, but it is a long trip, and I ain't planning on stopping in bali or Kuching, but who knows. Maybe i won't even leave. I've been talking about it for ages.
. . . but I do have 31 oranges, and that counts for a lot.
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