Originally Posted by pistonbully
Learn to sail, I live in Colorado and I plan to take the A.S.A Basic keel Boat course and Coastal cruising course to get my liscence and be able to sail up to a 30' on my own. There is a school in denver that offers the two courses at a really good price.
One point to consider is that you don't really need a "license" to sail non-commercially. Particularly to sail your own boat. And certainly not a license by boat size. I think most states require you to take some sort of boater safety course, but that's pretty trivial compared to ASA 101. The ASA or USSailing certificate series can look good on a sailing resume for chartering, but it isn't even required for that. (Outside of certain parts of Europe that want an International Competency Certificate)
That's not to say you shouldn't take the course; the ASA class is a good start.