[Gary M]

I do not live in the area but I would think any time between now and next years hurricane season would work. You will get a lot more wind between now and March.
As for Cuba, I don't think I would go there. There was a Canadian registerd boat that lost motive power near Cayo Coco about a year ago. They called for help but no help came. They eventualy went up on the sandy shallows and ther boat was pounded to bits.

The crew were essentially arrested. They let them return home in a few days.

Being Canadian I have traveled to Cuba several times. Other than Havana and Varadaro there are not many places to put in anyway.

Also they have virtually no maintenace faclities. If you need a bolt you will have trouble finding. it.

Gary