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Old 01-29-2012
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Seems to me you've got things well thought out, you have a reasonable time frame and a really good transitional plan.

The one thought that occurred is that given your stated 'not across the pond' mindset, when it comes to the Caribbean boat you might want to try to find a boat already in the chain (a newish ex charter perhaps) when the time comes. The 1000 miles to windward from Florida to the chain is a tough slog - it might be easier to 'cross the pond' ... This plan might exclude your C42 (great choice, btw) as we didn't see too many of those down there, seems the mainstream brand in the charter trade is Jeanneau - but I've like what I've seen in some of those boats.. certainly the 3 cabin requirement can be met that way.

Your interim 30 something Chesapeake boat could easily do the ICW and a few seasons in the Bahamas before heading east...

... but please don't bring up the likelihood of being retired in your 40s again...
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1984 Fast/Nicholson 345 "FastForward"

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Last edited by Faster; 01-29-2012 at 02:18 PM.
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