When daysailing on San Francisco Bay, we tend to stay out of the dirty air of our little islands, taking them on the upwind side and not worrying about the possibility of being driven on to a lee shore. In the large-scale world of the Caribbean, do you still keep upwind of the islands for clean air?
John Kretschmer responds:
You raise a good question about staying out of the dirty air in the Caribbean. Although it often blows like stink in San Francisco Bay, the difference in the Caribbean is the sea state. There is no doubt that the substantial lee created by many large islands creates dirty air, indeed, they often snuff out the wind completely. It is amazing to go from sailing in 25 knots to virtually nothing in a matter of yards. Still, the problem with going upwind off the islands is that there is almost always a large sea running, which really compounds the lee-shore situation, and so there just isn't much room for error unless you plan to get a lot of sea room.
Also, almost without exception, most of the really nasty hazardsi.e. reefs, rocks, wrecks, etc.are on the windward side of the islands. Therefore, my usual policy is stay in the lee. One thing you can do is stay far enough offshore so that the breeze that does funnel down the hillsides and reach you with some umph. In addition, you can sometimes use the land breeze or katabatic wind by sailing quite close to the shore since most Caribbean islands have relatively deep water.
I hope that answers your question.