Get a Mac 26 with water ballast and 65 hp OB. You could trailer it anywhere. Take it Florida, sail the Keys for experience. Watch the weather and hop across to West End in Bahamas UNDER POWER at 10 kts then sail the Abacos. I have a friend in Marsh HArbor and that is what he does (he lives on it) and he takes it further down all the way to Cat Island and if he can get there then it is easier to get to Georgetown.
Smaller boat, lower costs, much lower. You could even take your trailer across to Marsh harbor and keep her on it to save money.
Get tired of Abaco, go down to Eluthras and then Exumas, island hop to Turks and Caicos and then to Hispaniola.
Suggesting the Mac26 will get me accused of blasphemy but it is a far more practical boat than the Norsea27 and I maintain is actually a safer option as it can float in almost no water allowing it to be beached or moved into very shallow anchorages. At 10-12 kts with the big 65 hp outboard, it'll get you to safety in a hurry while the heavy boats are plodding to safety at 4.5 kts.
Good used Mac 26 will not cost too much.
I swore I wasn't going to do this but this was the last straw....Having read quite a few of your posts, it would appear that your standard response to any questions is "Get a Mac 26 with water ballast and 65 hp." It does not seem to matter what the question is. From "What kind of boat should I buy for daysailing?", "What kind of boat should I buy to cross the Atlantic?", "What kind of sail boat should I buy to do a great loop and save a lot of fuel?", to "Does this tie match this shirt?", your answer is always the same chorus "Get a Mac 26 with water ballast and 65 hp."
It does not matter how irrelevant it is to the question. It does not seem to matter whether you have thought through the question or considered the fine points such as the question involves crossing 1,800 miles of open water and how is a Mac 26 going to carry that much fuel, or the question involves crossing some pretty treacherous waters, or that the question involves a family of four, and so on; your chorus remains "Get a Mac 26 with water ballast and 65 hp."
And it would not be so bad if your answer actually made sense in most of these cases, but it rarely if ever does. And when someone calls you out on it you say that they are boat snobs or prejudice against Macs. Years ago I worked for a company that sold trailerables, commissioning Macs and Ventures and teaching people to sail them. They were slightly better built than some of the options out there, but not as well built as most normal sailboats of the day. In looking at newer Macs, they don't seem to get any better than they were back then. I have seen them try to sail in a broad range of conditions, and their sailing capabilities are poor, and approaching dangerous in a blow.
So, while I don't know why you think that a "Mac 26 with water ballast and 65 hp" is the Swiss knife of answers, but I would suggest for your own credibility that you at least try to filter your answers so that they at least sound plausible.