I am surprised that no one has chimed in yet on your plan. The
Carribean has great sailing, but if you live in
California, there is also great sailing. It is somewhat different between Socal, and Norcal, but you can gain lots of experience on the
west coast. Small boats are cheep right now, so you might want to buy a minimum
boat and go sailing/weekending with the
family, while you learn , and make your
mistakes on a small, easy to
repair boat. You could even buy a mini cruiser, and
cruise a
winter in
Mexico, and then
trailer it home.
Mexico is a very good
learning ground. I purchased my last 2 cruising boats at long distances, and while I was already pretty experienced, it made outfitting very difficult. Instead of dreaming about how you are going to live, you might try living your dream while you are
learning. It is not a bad way to go.____Just my 2 cents worth. _____Grant.