Hi Ellen... I've sailed all the areas you mention, and many more, except Croatia. Planned a trip there this year but had to cancel for non-covid reasons. I've never been on any sailing holiday, to any destination, that I didn't enjoy. Caribbean is definitely best for pretty much guaranteed wind usually at reasonable strength. The Med is often no wind or too much wind but the rest of the experience makes up for the less than perfect sailing.

Right now though I'm not going sailing, or on any vacation, that requires me to go to an airport and get on a plane. Fortunately I don't have to get on a plane to get from the UK to Spain so I'm planning to charter from near my house in mainland Spain and sail to the Balearic Islands (Ibiza, Formentera, Majorca and Menorca, the nearest of which is only around 50 nm) next spring. I have sailed Majorca previously but none of the other islands and am really hoping this can go ahead.

If I was in your location I'd be planning on picking up a boat in Florida and hoping to get to the Bahamas. If the Bahamas won't let you in at the time at least you should be able to sail the Keys.