Hi Lisle, We were in a similar situation almost 2 years ago before we bought a C&C 34 for family cruising.
I'd never sailed a keel boat and started looking for a boat. My wife had never sailed (except when I flipped a laser in a gale at the resort on our honeymoon). Since we bought the boat we've had great family adventures for the past two summers with our kids who were 3 and 6. In hindsight, I wouldn't be as worried about a bigger boat. We agree that we're glad we didn't go with anything smaller. [To think I almost bought a Catalina 22 at one point]. Now we're starting to look at bigger boats... problem is the attachment and investment into the 34' at this point. For this reason I'd recommend buying something that has the size and extras that you might want in the future (perhaps updated rigging, nice gel coat, repower, rewire, good battery setup, diesel heater, furling jib, windlass, good sails, jack lines, masthead antenna, electronics, dodger, canvas, BBQ, , ...) The cost of these may not be reflected in the market prices. To get up to speed, I took some cruising courses. Bought the boat and hired an instructor for a few sessions to help us learn the ropes on our own boat. We still have so much to learn and we've already learned so much. We can manage the 34' and everyone has fun. The best weeks of our summer were spent at anchor in Desolation Sound. Cheers, Jeremy C&C 34-1 #041 Vancouver BC
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