By getting a boat. Getting on someone else's boat is good too, as you can get experience and learn from them. Sailing is easy - you don't need to win races when cruising around the world, so the finer details of trimming will be wasted on cruisers (you can always pick them up on the way). Navigation and traffic rules shouldn't be hard to pick up for the average HN crowd, although yachties like to make a fuss about it.
I did a few RYA training things that cost a lot of money and got me some papers that nobody ever wanted to see (they're important if you want to charter a boat though). You can just buy the syllabus and gain the knowledge by online learning or video courses instead. I recommend going that route - the knowledge in the syllabus is important and very useful. The formal course in a classroom and the certificate are not. Practical knowledge is gained only by going sailing, making mistakes and learning from them, but it helps if you know the knots and the parts of the rigging beforehand.
But the real learning only begins when you get your own boat and have to fit it out and keep it going. Boat maintenance is hard and there's a lot to learn. You can initially substitute money, but that stops working once you get to remote areas where there is simply nobody else to pay to fix your boat and you will have to do it yourself or give up. Many decrepit boats in remote locations are on the market very cheaply for exactly that reason.
Do you recommend Jimmy Cornell’s world sailing routes books? I have about $100 worth in my wish list, spiral bound, I’ve been waiting to purchase until closer to departing on a circumnavigation.
They're great, but you'll end up looking at them once a year when you do your passage planning for the next season. Excellent resource, but a bit pricey and heavy to sail around with.
Finding a boat on a budget is easy. What is not is finding a harbour post to moor it. At least here in south of France, this can get really expensive and you may have to wait for years before getting one.
You might be able to find a sailing co-op in your area. I'm a member of one that requires 30 hours of volunteer work, which you can gain experience in a wide variety of things - fibreglassing, painting, plumbing, electrical, rigging, etc.
We've got a fleet of 6 27' - 30' boats which are great for day sailing and week long vacations.
1. Watching a lot of YouTube, see my list of channels in another comment, and the note about not believing everythin they do is correct.
2. Joining the local dinghy sailing club. It's cheap, and although I don't really care about racing the skills were mostly directly transferrable to larger boats. Plust contacts are really useful.
3. Get on other people's boats as crew. I own a 43ft yacht, my friend sails it with me. It costs him nothing :)
Later, when you have tried it out and got some experience, take your Day Skipper (RYA) or equivalent course (the ASA in the US runs some). You should at this point have a reasonably good idea of your skills.
At some point in the process, start looking at yacht listings. Yacht World would be a good start. Get an idea of the market. You will work out how much you need to save, and what sort of prices are reaonable.
get classes, pretty unexpensive. After your first 5-7 days when you learn basic skills you will receive plenty of invitations to crew.
Not unlike the corporate world, too many chiefs, not enough workers. Good crews are in high demand (and you can bring significant other, friends).
Lots of owners are clueless.
Lots of big boats are looking for crews, typically an ocean crossing. Think Panama-Tahiti. Expenses, including flights, paid
