Sea&SkiPJ - I’m landlocked Atlanta, so would prefer something in Florida or the Caribbean. I hope to be retiring soon and plan to move to the coast.
One other question about tips for the crew: if 10-20% is standard, that would mean several thousand dollar for a crewed charter. Does the tip necessarily have to be in cash? That would be a lot of cash to carry around for the week.
I've taken courses with Black Rock Sailing School and they're pretty good. They have a base in the USVI, but I don't know much about that operation. They have nothing in Florida. I've had positive feedback about Blue Water Sailing School, but never took classes with them. You might hop onto the American Sailing Association website. They list all of their affiliated schools in Florida. You can see if anything meets your needs. If you're ever in New England, on the other hand, go to Narragansett Sailing, they're fantastic.
I'm sorry I can't help with the tipping question; I'm a bareboat sailor.
