Would not worry about Hurricanes...most miss the island historically. Also Ivan as a Cat 5 hit the island years ago and only caused one death which I heard was preventable. It is fairly hurricane safe. Of course we all know you only need one. It is interesting that my insurance
was more expensive to keep my boat in Key West
than it was in the Caymans. Marinas are expensive, the cheapest one is called the Yacht Club which is not really a Yacht Club in the true sense. There is a very active sailing club at a different location. Then are all off the North Sound that you enter through a few channels along the barrier reef. These channels do get breaking waves in the winter months with the Christmas
winds but are manageable. During those times going around to the west side of the island provides an idyllic anchorage with swimming pool like water. Also there are moorings in Georgetown
that are well maintained and free. Mostly avoided that area because of the boat traffic and have personally counted as many as 6 cruise
ships anchored at one time !
The problem I found is the 12% duty on your boat if you stay there over a year. Initially they give you a few months necessitating continued paper work
for extensions then for around $1000 you can be granted a prolonged stay up to a year then you would have to pay the duty. I did keep my boat there for a year and then left however thought about just going and returning from time to time which may have worked by resetting the clock. There are two boatyards
that can haul your boat if the need arises and I suspect they would allow you to do your own work. As opposed to keeping your boat at a marina you may want to check into renting
a private dock
from one of the many bulkheaded canal
homes and lots available. It worked for me and was much cheaper than a marina. The people are wonderful, great diving
are plentiful just no spearguns!!!! Oh yes and Cuba
is just an overnight sail! Let me know if there are any other questions.....have fun.