Seeking input to go from Scratch to Captaining

[SeaLifeSailing]

This is not a pitch for my school, but I agree completely. When you go to an accredited school, you take a class with a professional instructor with a curriculum assembled by experienced sailors and educators.

Do a little homework and ask around locally to find the school that's right for you. Nothing wrong with asking to meet the instructor in advance, either, to figure out if that person's personality and style will mesh with your own. Reading books is a great start to understand what boaters are talking about, but there's no substitute for time on the water. If your budget doesn't reach to a cruising school, perhaps try a day-sailing school or begin by learning to dinghy sail with a local club. If you really want to spend time on keelboats, volunteer to crew at a local yacht club.

But the only way to truly learn to sail is by going sailing on a boat, in the water.

As a professional instructor, I can tell you that it's harder to teach someone who's read a stack of books on sailing than someone who's read one decent textbook, because the heavy reader will have a whole pile of theoretical half-knowledge that isn't grounded in practice, and their 'knowledge' winds up getting in the way of organic learning. What's more, they'll be asking questions about advanced subjects that simply aren't relevant at the beginning stages learning to sail, before having a grasp of the fundamentals.

That's my two cents', anyway...

Originally Posted by Zanshin

There are numerous books out there to help you get started, even the "Sailing for Dummies" book is a good start.
Hand-on experience is more important, though. You should check out clubs and organizations in your area to get some familiarity and training without having to spend too much money.

If there are a lot of sailboats around then going to the docks before races and regattas and asking if anyone is looking for inexperienced crew ("rail meat") will get you started, once you've done that you'll be able to make contacts and get even more time on the water.

Personally I would prefer going to an accredited school and taking a class - the curriculum will be put together by professionals and the class taught by one as well. It might be more expensive than the other options, but will most certainly get you to your goal faster.