Sadly, I think the OP was overwhelmed by the response. He may have meant Bahamas when he stated Caribbean.
Miami to Bimini to
Lake Worth in a well maintained C22 isn't unreasonable in my opinion but ONLY if you can pick your weather. If you can't wait you may have to fly back instead of chancing it. We get some big fronts in spring.
It sounds like your off to a great start. Many good suggestions were proposed in the thread. To add to your list I would suggest;
transom scuppers if your year model doesn't already have them,
mechanical fasteners for the
companionway hatch boards and back up board,
a one piece
rudder with the kick up as a back up,
lines led aft,
improved pop top hold downs,
verify your
battery mounting is faultless,
We removed and our keel pivot
gear for close
inspection and replaced the bolts regardless of condition
Epoxied spacers to the keel to lessen excess play.
Replaced the chainplate
hardware. It was removed for rebedding and one bolt failed being installed due to porosity
corrosion. It was not noticeable during
cleaning though would likely have been detected with dye testing.
The C22 is a great boat in her conditions. We found it uncomfortable outside when the average wave height hit about six. It relies a lot on structural stability with her flat bottom and the heel angle can be offsetting outside. Coming back through the inlet can be dangerous if you cannot pick your tide. The
motor can be useless in some wind/wave combinations regardless of shaft length. You can have a really bad time if you don't plan well.
People cross in kayaks (see " crossing for a cause")
When discussing it with the old salts a common suggestion was "Just don't cross on anything that starts with a N". Very good
advice. You don't want to ride the elephants in a
Catalina 22.
.. and of course lots of experience with your boat.
Best Luck and Best Regards