Originally Posted by Oaksail
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.
I agree with Oaks,
When I decided to buy a boat I was initially looking in 30' 35' range. Then when I found my YC and started talking to other sailors and a few online friends everyone said "get smaller to learn on" Well I did. Wound up with a very nice Hunter 23, it was a lovely boat, and I liked it for what it was. But I sold it after 11 months and bought my Oday 30, The money I spent on the H23 could gone towards a larger boat at the time. Now that things have changed I may never get a larger then 30' boat but at least I have something I can spend real time on and have the comfort and facilities that make staying on the boat much more enjoyable.
Holding a tiller, reaching over the transom, flipping the gears from fwd to rev and trying to dock was not my idea of fun on a smaller boat.