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Lookin' for an excuse ...
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I've done that trip a number of times delivering sailboats. The best way to go is between the Bahamas and Cuba through the Old Bahama Channel. You will be sailing west/northwest, which means you will have an almost dead, down wind sail. There tends to be traffic in the channel, so you will want to be sure you have experienced crew who know what to look for. Also, it seems every time I go through there, I get boarded by the Coast Guard. They don't make you stop. They radio first and then approach with an inflatable for the "at speed" boarding. Last time I got boarded they gave us some bread and a newspaper before leaving. Not bad!

Once out of the Old Bahama Channel, if you are going up the east coast, get in the Gulf Stream for a sled ride to your destination. If you are going up the west coast, stop in Key West for a breather and then head on to your home port a day or so away.

Here's a picture of the Coasties and me the last time I went through the channel.
Uniform Crew Team
 

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Lookin' for an excuse ...
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158 Posts
The approach to the Old Bahama Channel goes just north of Puerto Rico and the Dominican Republic, both of which provide a place to duck in out of weather. At the east end of the channel is Great Inagua and Matthews Town with a fairly good harbor. I've been in there, and it can provide a place to sit out bad weather; although I would be concerned about tidal surge in a strong storm. The harbor is very small with a narrow opening to the west.

Once you leave Great Inagua behind, it is approximately 360 NM to the Cay Sal Banks and another 150 NM to the Florida Keys. I have looked at charts for the north Cuban coast in the past and I'm not sure I would want to try to go there in bad weather.

Going up the east side of the Bahamas puts you in open water for several days also. You aren't going to escape that. If you are overly concerned about your exposure to bad weather, the time frame you are planning for the delivery is probably not the best.
 
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