Recommended cruising boats
Jeff makes a valid observation, altho'' of course the trick is to fold in all these variables (build quality, size, layout, cost, etc.) into some choices that are desireable to the person asking the question.
My reading of the original post is that a Caribbean cruise is being considered. I would be VERY reluctant to take a Hunter 37 cutter down there, only because the 37''s I''ve seen (different from the ones Jeff''s seen) are poorly constructed, suffer from bent rudder posts and bent shafts even on the ICW run, and would not enjoy the heavy windward motorsailing, while the hull/deck monocoque structure is worked over and over by the opposing swell & wind waves. Just about anything can get down there, of course, but the boats mentioned ("... Island Packet 35, the Tayana 37 and perhaps a Morgan 38") are all IMO of substantially better construction and more suitable for that kind of run without undue stress on the crew.