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I haven't sailed this for over a decade so don't rely on my comments... but here goes.
If you start up in Rodney Bay do a stop in Marigot in St Lucia, it's one of the most delightful places in the Caribe. It's a relatively short sail from Rodney Bay and makes a perfect lunch stop.
You may need to sail west a bit to escape the lee of the Island and get some decent breezes. If you stay in closer you can have a delightful sail in flatter water and more moderate winds.
Drop in by the Pitons... they're cool.
Castries in also a funky Caribbean city.
Defintely get Chris Doyle's Cruising to the Windwards. He'll tell you everything you want to know.. current information and who knows... you might run into him down there.
Your skipper is all you need if he is competent as I am sure he is.
I don't recall the conditions between St Lucia and St Vincent other than it being a day's sail in the trades.
jef
sv shiva
There's some interesting things to see ON St Lucia
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