As you stated not a lot of sailboats to choose from in the CI if any at all.
Also have you thought about where you will keep the boat once there?
are not inexpensive however my suggestion is to check out the daily newspaper for someone advertising a private dock
. Many canals with bulkheaded docks but again have to investigate.....would start sooner than later.
Hopefully someone on this forum can go with you, would not suggest going on your own with limited experience. May also want to hire a captain
to bring the boat down for you. I would personally take the eastern route
through the Bahamas/Windward Passage
then stop in Port Antonio Jamaica
and on to the Caymans.
The moorings in Georgetown
are free but these are weather
The North Sound would be your best bet to keep the boat but would suggest getting a local to guide you through the reef and there are many uncharted low spots once you are inside.
I have kept my boat there in the past and know the island well so if I can be of any assistance let me know.