Well then, Amanda, just about any kind of time on the
water would likely help you get closer to your goals. Even the bad captains can teach you, though some of them may teach you what not to do!
"Dockwalking" is something of an art of using on-line (or dead tree) crew lists at yacht and sailing clubs, checking bulletin boards at marine-related businesses, visiting clubs and
marinas, hanging out before races, volunteering for
race committees and helping with sailing
events, and chatting up sailors wherever they gather, to bum rides, learn boat care, etc.
There are also services where you can sign up as crew for longer voyages, though some basic experience and
training would make you more marketable as crew. Also, there are some steps to take to
research skippers more carefully for longer voyages for
safety, good behavior, and compatibility.
Sailing lessons can be a bit pricey, but may be very worthwhile before spending
money on a boat of your own. Sailing co-ops and clubs may be less expensive and a decent way to get boat access at a reasonable
price.
STCW and US Coast Guard or equivalent foreign licensure (the professional end of Yachtmaster, etc.), moves into working in the
marine industry, of which there can be a variety of paths --
cooking and hostessing on yachts, or apprenticing as
deck or
engine crew, or going to an academy to become a merchant
marine officer, or working on smaller craft as a
boating instructor, water taxi operator, tugboat crew, etc. Some of these pay poorly and others require long hours, but such is life. Some schools help people learn to pass exams for licensure, but these don't substitute for experience -- and a lot of on-the-water time is also a requirement for licenses.