I think your plan sounds reasonably well thought out. I have a few notes.
I am not sure I would use a Grampian
23 for the Caribbean
, I've spent quite a bit of time on the G23, when I was a kid I cruised on my dad's (nearly new) G23 on the great lakes
. Fine little boats, but lightly built, Im not sure I'd be thrilled about being 50 miles off shore in one in 6 or 7 ' Caribbean
seas and sustained winds of 20 or 25 knots. That sounds kind of scarey to me.
My last boat was a Grampian
30, which I paid $8500 for, she was a nice weatherly boat, but I would not have taken her to the Caribbean without probably close to $10k in upgrades, which would put you in the ball park of you're 10-15k range. I'm sure you could find a 26 or 28' boat that is safe, comfortable and in your price range. If I was in your price range, I'd be looking at a nice 26 with standing head
room and possibly a brand new or nearly new outboard
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