The University of Washington Yacht Club in 1992 was where we started sailing. Taking the University's 22' boat up to the San Juan Islands during summer break totally hooked us. Definitely our best vacation ever, even though we had no heat, running water, standing headroom, or really much of anything acccomodation-wise.
After college we bought a house the first year and a boat the second year. Our first boat was a Catalina 34. We loved her much and sailed her a bunch. Soon we realized that owning a house and boat both was silly; all our time was at the marina. We decided to "go cruising", and planned to build a steel boat.
A little thought on that one made us realize that we ought to do what we do (build software), and let the boatbuilders do what they do (build boats). We sold the house, sold the Catalina and bought the Baba all in one very insane weekend. We had found the Baba 6 months earlier for sale, and were finishing up the remodel work on the house. In the meantime, the Catalina dealer knew we were going to sell, and found a buyer without putting the boat on the market. Somehow it all worked.
Then I decided I really did need to learn how to sail better. Corinthian Yacht Club in Seattle has a "Rookie Rally" every year, and that's where we ended up. We knew that racing was the absolutely best way to learn to sail, and if I was going to sail the world in our new boat, I really wanted to know what we were doing.
Racing has been such a blast for us. We've made lots of life-long friendships and had tons of fun. And in the end, I think we learned a bunch about sailing. Now we're in "cruising mode", so the racing is left to fun matches with Puget Sound Cruising Club.
But now we're headed out to the open ocean, where I know nothing about sailing, so I guess it's time to start learning again!
What's next? Sheesh, who knows? We're not about "having stuff", we're about "having fun". In the end we'll not have a string of nice cars or grand houses to remember, but hopefully we will have lived a life of awesome adventures with great friends and family.