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I'm looking to do exactly they same. I know of two couples who are doing similar. Thought the one is more into windsurfing (I am also a windsurfer so would include this in the list of activities whilst sailing), the other is doing it with two children and are currently exploring southern baja. Both of them are doing it from cats so I guess have more options with anchorages. There is also a great movie called 180deg South which documents a surf trip on an old sail boat down to Patagonia.

I've also recently read a review for a book called Swell, which sounds like it could be a good read on the topic.
 
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