I went from a Seafarer 22 to a Gulfstream 232. The ride of the 232 was noticeably better.
I have ridden on a friend's 258 Journey and the ride seems a little better than my 232. I believe the narrower 8' 6" beam of the Journey helps in a head or quartering sea. The 232 is 9" 3', remember, so it's wide for it's length, therefore has a wider "footprint" and pounds a little more than the 258.
If you don't want to make a significant jump, the ride difference you'll achieve will be noticeable, maybe but not nite and day. The heavier and bigger, the better.