Learned the basics at about 10 when Dad bought a 1970 (?) Bristol Corsair 24 in New York. Passed the USCG basic boater course, with my folks, at that time. Crewed on a Turnabout a few times at my grandparent's in Mass over the next few summers, plus annual cruises on the Bristol. We moved to Oregon in 1977 and Dad left the boat in Maine; I stayed here when they went back in 1981.
Fast forward 22 years, to 1999; I spent a week sailing with Dad on the Bristol. It all came back pretty quickly though I almost dumped him overboard because I turned downwind instead of upwind in a gust - he'd installed a wheel in place of the tiller I'd grown up with and I reacted by pushing it away without thinking. Oops!
A few years later he shipped my sister's old Laser out with some furniture. You can (re)learn a lot in a laser including that it's a young man's boat. Next up was a Catalina Capri 16.5 which had room for my wife and one or two grandkids. That boat taught me about reefing and making sure you explain things to your (novice) crew before it hits the fan. It also taught me that when the wx calls for 20+, and the only boats going out are 24 footers and up, maybe you shouldn't take a little centerboarder out too. 15 months later we bought Verboten, our Catalina Capri 22.
Verboten has probably taught me more than all the other boats combined. She's got the tall rig, so she powers up quickly, and, as a former racer, she came with more sails and lines than any boat I've ever been on - windward sheeting traveller, outhaul, cunningham, vang, boomkicker, 3 jibs and a foil, spinnaker & pole, adjustable backstay, twings for the spinnaker sheets. Plus a 4' fixed fin keel that I really don't want to thump into a submerged stump at the lake or get snarled up in kelp cruising in the San Juans (once was enough, thank you!).
Verboten still has a lot to teach me in 2011, I think. I've done some sailing in 20+ winds but not enough that I'm really comfortable. I know the boat can handle it if I get the right sail combination up, so I just need to bite the bullet and go play when the wind comes up. I also want to learn to fly the gennaker another sailor loaned me - I sold the symmetrical spiinnakers and pole, knowing I'd never use them; the gennaker seems much simpler and more user friendly than a chute & pole, especially since I'm usually sailing short handed.