Re: Jumping from race boats to cruising
We're mostly looking at older C&Cs in the 35-foot range. They were well-built, pretty (a high priority), fun to sail, and roomy enough for our purposes. They also fit our very limited budget. I doubt a multi-month cruise is in our future, but the boats are adequate for that, with a little work.
Most of the time we'll be going out after work for a sunset sail, or taking off for a long weekend. Though I'd expect that we will be aboard for a week or two at a time in Maine or the Chesapeake every year. The C&Cs are ideal for that.
And almost as important will be sitting on the porch at the YC sipping something cold and admiring my boat!