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I know the trade winds leaving Turks are going to be constant but what happens when I get between Cuba and the Bahamas? Any advice on making this sail? I fly into Turks next week (weather permitting) and should start sailing next monday (July 27th).
 

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haven't done it myself, but it sounds like a down wind or cross wind run with the Gulf Stream in your favor.

When was the diesel last serviced by a competent mechanic?
 

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May I suggest a different route? Sail up the island chain to the Exumas in deep and protected waters and then cross to Bimini and then the FL Keys. This will at least give you some bail out options if the weather gets bad as well as easy sailing in more protected waters since you are on a lightly built boat with unknown issues with engines/systems facing you it seems.

Whichever route you take...please post a report afterwards as it should be an interesting trip.
 

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If you choose to go northwest from T&C to KW, its about a 525 mile run from Mathew Town on Great Iguana, through the Old Bahama Channel with a roughly 10 mile wide channel between Labanderas Reef and Cayo Cruz, Cuba. Through the Nicholas Channel south of Cay Sal Bank you'll be fighting the Stream. It's doable, assuming the yacht is in good shape, and you get a good weather window of 4-5 days, but it might be wiser, and will be easier, to run north through the Bahamas as previously mentioned. Once in the Old Bahama Channel you're committed, come what may. Your only options then will be whether to go northeast of Caysal, through Santaren Channel or northwest, through Nicholas.

FWIW...
 
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