I went from a Newport 28 (@7,000 lbs, fin keel) to a Gulf 40 (@22,500 lbs, full keel). I won't repeat all the great things others have already said (OK, becuase honestly I didn't read each and every line, so if I am being redundant... sorry), but I believe one of the most important elements in moving up to a larger boat is confidence. And I'm not speaking of false bravado style confidence. I mean knowing that you can handle the boat with aplomb. In a Buddhist sense, you need to "become one with the boat", in that she is an extension of your body and mind. That sounds weird even to me, but it works! I always suggest to people that they get to the point with their "smaller" boat that they can do anything with it they want, in (just about) any circumstance. If it takes practice, then practice. I actually found the bigger boat gave me a sense of confidence in her, probably due to the 60 hp engine and larger screw, which made maneuvering in tight quarters fairly easy. Prop walk is your friend!
I also have a friend who went from a 26 foot fin keel to a Formosa 51. ANd his nickname with the first boat was "Captain Crunch"! But the transition went just fine, and he moves that big old gal in and out of places like a pro. I think it's because he is VERY confident...
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"Always approach the dock at the speed you wish to hit it."
1978 North Sea 33 Pilothouse Cutter (Ta Chiao)