I did some on line research and one of the websites I found easy to navigate and was chock full of information is SailingVacations.com. There is a place on the site for people wanting to learn to sail -- you! The only thing about this site I didn't like was I couldn't find actual prices, even on the page that says "Pricing."
If this is something you would like more information on, I would be happy to get the information from my friends regarding how they arrange their sailing vacations (yes, some of my friends have done this more than once!).
If I were interested in integrating sailing into my life, I would take this kind of vacation. It would serve multiple purposes; I would be having a great time, I would be finding out what it is really like to live on a sail boat, and I would have the chance to find out about other professional opportunities. I call this Orange Road a win-win-win situation!