endeavour, hunter, irwin???
You are asking a whole lot of questions and only providing scant info that would help someone provide a meaningful answer. (It would be helpful if you explained how many people were going with you, what your experience and physical condition is, how much your would like to budget, are you adverse to slow boats or lots of motoring, are you prone to seasickness and so on.)
To deal with the basics, the three manufacturers that you mention each have produced models that might work for what you plan to do and a whole lot of models that would fall pretty low on an experienced offshore sailor''s list of likely candidates for these venues. If you were looking for an ideal boat for the venues that you mention, it would ideally be a boat that offers a wide range of sailing capabilities (light and heavy air plus anything in between), shoal draft, good ventilation, good engineering, and generous tankage. The Carribean, Florida and the Bahamas are tough on a boat . All three expose boats to an environment that really ages a boat quickly(lots of sun, high salt content, and often rough conditions). The Carribean is known for its strong winds, the Bahamas for its short chop and rolly conditions and Florida can offer almost any kind of condition at any time. Boats in these areas are used year round and will often have two or three times the number of hours of a northern boat which is out of use for half of the year.
If these are the three models that somehow made it to your ''short list'', then, with all due respect, you have a lot of research to do and the internet is not necessarily going to give you a clear answer. For one thing, most of your questions do not have one universally right answer. The kind of boat that I would buy for those venues would be very different than the first choice made by other equally experienced sailors. We each bring our fears, goals, experience, and priorities to the table and these shape what our ideal boat will be. No one can really answer this question for you in a way that will actually be meaningful for you, at least without a whole lot more discussion.
What I can say is that in a general way, the majority of the products by the three manufacturers you mentioned were ''value'' oriented boats. As such they offered a lot of boat for the dollar when used as coastal cruisers but generally do not offer the accomodations and engineering that one would associate with an offshore or a even well rounded design.
So while many people have sailed a lot of miles in less than ideal boats, with the kind of agenda that you are suggesting, I suggest that you might at least try to tie down the desirable characteristics of a boat for this kind of sailing and then begin your search. O suspect that your short list will be extremely different than the one proposed.