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Dallas, Try googling SJ23 to find users groups. You might find out if folks have cruised them in the Keys and elsewhere. I know that people who sail the Catalina 22 have cruised the Keys, over to the Bahamas and in all the inland and coastal waters of the USA. I don't know the SJ23, but the C22 is probably similar with 500# swing keel, displacement of about 2300# dry. I think the biggest problem, since you already know how to handle winds up to 35 knots, would be big waves. And the 9 hp o/b should be okay except in a strong contrary current. Pick your weather windows and time your transits thru channels according to the tides and you should be okay.
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Sailing isn't a matter of life and death. It's much more important than that!
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