Join Date: Aug 2008
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I agree with Eryka (especially because she's actually out doing what you want to do) - get the bigger boat, making sure to have a quality survey done before you buy.
My first boat ever is a C27. It was sail-able when I got into it, but it needed TONS of work. It's been great learning to sail it WHILE working on everything that needed fixing (plumbing, electrical, cushions, motor, you name it). And 27' is not a big deal in terms of "big boat". You get used to it real fast.
It takes money to pay slip fees and repair/upgrade stuff, but the return is awesome. You're learning everything on your own boat. That way you'll know exactly when you and it are ready to push off for the horizon.