I was in your same situation during the summer of 2010. No sailing experience, little boating experience. We had traveled quite a bit with the kids and decided to something different. We bought a 30 ft CS just as she came out on the hard in the fall of 2010. Spent all winter fixing her up and learning everything i could. Youtube can be your best friend when learning something new. Mainesail will be your other best friend. Docking and maneuvering was alot easier than i feared. Sailing, I'm loving it! I think a 30 footer is perfect for us. If you are confident, sensible and have a grip on common sense GO BIG as you can.