Welcome, Pygar62!
When we went Bahamas/Caribbean cruising a few years ago, I had a ‘fair’ amount of experience on sailboats of various sizes but it was mostly daysailing or tame yachtclub
racing and mostly on other people's boats. My wife had zero. We read a lot, shopped around, bought a
boat, and spent 4 months refitting and practicing. After 4 months we took a ‘practice’
cruise was from Tampabay to the
Dry Tortugas and the Keys. As we were about to
head back from
Key West a
weather window opened to cross to the
Bahamas. Everyone else there was going, so ... we made a couple of
phone calls and we went too. We didn’t come back for over 2 years.
We met plenty of people who had been sailing in one form or another for years before they decided to go cruising. But we met many others who didn’t have any experience at all until after they decided to go cruising. They usually didn’t just buy a boat and go - although these people did:
bumfuzzle chronicles.
The conventional view is take lessons/courses, and crew on other people’s boats, and
charter, and buy small boats, and then bigger boats, etc. Most people we met did some of those things, but I don’t think we ever met anyone who had done all of the frequently recommended things. Most people who don’t have pre-decision sailing experience and actually
wind up cruising, find a way to shortcut the
learning curve. And, regardless of ‘sailing’ experience, all first time cruisers quickly discover that they still have lots to learn and the only way to do it is to just go cruising.