How to buy a sailboat
I agree with Brian: try and get into a sailing club or charter type operation before you buy. We did (in CT), and it made a big difference in how I approached my purchase. I found out what I liked and didn't like in a couple of models, and what features were really important to my family. For instance, we sailed mostly on a Catalina 22, and learned that my wife really wanted a boat with an enclosed head, something sorely lacking in the 22. Also, despite my desire to buy the biggest, most comfortable boat I could afford, I dispassionatley realized that I would be mostly daysailing, and a big cockpit was more important than comfortable sleeping and cooking facilities. I learned all this from very limited experience with a few boats. Get out on as many boats as you can and see how it feels to steer with a tiller vs. a wheel, roller vs. hank on sails., etc. Then you will be able to make an informed choice as to which boat is right for your family. As an aside, the 23-28 foot range you have specified really encompasses a large leap in types; above 23 or 24 feet, boats get a lot heavier and more comfortable below. Rare is the boat under 25 feet with "standing headroom;" rare is the boat over 26 feet without. If you decide that you definetly want to cruise and need accomodations in your boat, I like three widely availabe boats: the Catalina 25 (pop-top, fin keel model), the Catalina 27, and the Pearson 26. All are time-tested designs. Also, as general advice, I used the book "How to Buy the Best Sailboat" by Chuck Gustafson as a guide. Lots of helpful tips and insight. Good luck.
