Can anyone offer any advice on how to get started.

My wife , kids and I have a dream to cash out, buy a boat and sail the Carribean for a year. Obviously its not quite that simple, and so I need advice on how
much sailing experience I should get first,
how much of a problem are pirates,
how to deal with them,
ways to earn some income during the trek
must see destinations
any other advice you can think of.

If any of you can offer any advice on where to start, please do.
Thanks
Shawn