I started with a 33 footer on the basis that the movement was slower (I didn't sail until I was 38) and that mistakes at dock would be spread over a larger chunk of gelcoat. While I agree in principle, I moved to a 41 footer for long-range cruising...the 33 footer was simply inappropriate to modify to that end.
But I've kept her and still sail her and will, after a few years, likely pass on the 41 footer, because it's too much boat for the Great Lakes.
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