As a sub-40 ft owner of a Beneteau production boat...let me ask how many SMALL production boats are sailed over or across on their own bottoms. I'd venture to say not so many.
A larger Beneteau, Jeanneau, Catalina, etc....I'd take across the ocean, but not sub-40 ft.
WHY? It's only been the last 15-20 years that the size of the avg cruiser has gone up over 40' or so. A generation ago people were out there in boats in the mid 30 foot range. Tania went around in a 26' boat. Robin L Graham was in a 24' boat for 3/4's of his circum IIRC. And then moved up to a an Allied 33. Boats only got bigger b/c people decided they had to take so much crap w/ them. And sail handling got easier; electric winches, dependable furlers, etc.
I personally don't want something bigger than 40'. And I'll be glad to go offshore in something smaller than 40'.