I have three sailboats, well actually just two at the moment - I am in the process of buying the third - the Catalina 36. The first sailboat I owned (I have sailed many that I didn't own) was purchased used in 2006. It is a Hobie One 12 foot single hull single sail centerboard type. The picture below is of the Hobie on its trailer overlooking Lake Pleasant in Arizona. They used to be called Holder 12 before Hobie bought the design and changed the name. It is a good looking, peppy, nicely powered planing hull that can get going really fast. I've capsized in strong winds. There is no reefing so when the wind comes up, it's hang on for dear life and usually a spectacular crash not long thereafter. I've been trailering it to the various lakes in my state and taking pictures of each sailing adventure for a book I am writing called "Sailing Arizona." Arizona has a surprisingly large amount of lakes for our location thanks to dams and other management. I have to admit most of the time I've sailed in Arizona the wind has either been not enough or too much. There have been occasions where I've gotten some pretty good sailing in, but usually its either gusty or nothing. Still, I keep the Hobie One on its trailer in my garage and tow it behind a truck or motor home to "bag a lake" whenever I get the gumption to go on such an adventure. I've bagged like 8 lakes out of the 30 or so in Arizona worth sailing. The second boat [behind me in the picture above] is a 1985 Catalina 25 acquired in early 2007. I was up at Lake Pleasant outside of Phoenix (one of the 30 worth sailing) shopping for sailboats with my cousin at the Sailboat Shop. Nothing in their inventory inspired me. We went to leave. As we drove away, we saw a beautiful sailboat with white sails up in the parking lot sitting on a double axle trailer. Sure enough, there was a For Sale sign on the boat. I inquired. He said I probably wouldn't be right for the boat but invited us up the ladder for a look inside. It looked clean and cozy and reasonably roomy. A bit of teak and some nice features like a stereo with speakers inside and out. This boat was much nicer than anything at the retail outlet. I bought Singmeaway by phone as I drove back to the highway. The owner Scott and I spent months afterwards meeting on weekends at Lake Pleasant to teach me how she worked and how to operate her safely. Valuable lessons. I learned how to reef from Scott, among other crucial cruising skills. Scott kept the boat on Arizona lakes for all of its life. I aimed to take her to the Sea of Cortez. Scott was not particularly pleased about that and tried to discourage me numerous ways. After the training was over I arranged for about 3 weeks of vacation in May of 2007, went up to Phoenix, picked up the boat, trailered her to Tucson, spent the night at home, and trailered her to San Carlos, Mexico. It took a few days to rig and provision and I was off. Sailed to Guaymas on that first trip and back. Then went home to Tucson for a week, came back, and took a much longer trip to Kino bay, across the Sea of Cortez through the Midriff islands, and back. Awesome. I'll eventually share the pictures with some more details. Well, things kept progressing in my mind and one day I just went and did it. I found the boat that felt right on the internet, called the owner, and began buying a 1995 Catalina 36 MkII. It's quite a step up. Not a full-on blue water cruiser, but a well respected coastal cruiser that is moderately priced and well equipped for a variety of conditions. I'm leaving for final inspection and purchase a week from today. If I buy, I will be sailing it down the intercoastal waterway for three weeks of October vacation before mooring or dry-docking it and flying home from wherever I stop. I'll keep you posted.