Thanks for the replies
Jackdale and Faster,
I greatly appreciate the feedback. I'll have to look at the boats in charter. I guess I have been casually hearing (but not really acknowledging) that the jump off is a bit tough. Is there an actual 'route' that is the recommended track? What is the general method of doing the Caribbean?
One area I didn't mention is that at least partly doing the ICW is also interesting, but I wouldn't mind just getting a boat in FL, doing a refit for a few months, in conjunction with some test sails, and then head off through the keys and into the bahamas.