For BEST, I second the Nor'Sea 27. Also consider Dana 24 (and other smaller PSC boats). Both are trailerable boats that have circumnavigated. I don't think you are going to realistically be able to cruise the caribbean on 30 days a year - maybe you could do the bahamas (but even that would be pushing it). I know people who have done the Bahamas in a Catalina 27 and similar boats.
You really need to say what your price range is? What are your towing capabilities? Trailerable is a relative thing. Figure out what you actually plan on doing with the boat and buy a boat that can acomplish that goal.
Also have you considered chartering? If you really want to see the caribbean on a limited timeline that is the way to go.