Hello Oldhatt: I was up north fishing and finally 'home' again (Placencia) and saw your message.
We probably have a lot in common considering the similarities as to age, a mutual yearning not to 'sit to just die' too early and would like to end it all with one cool last adventure.
I left the U.S. 13 years ago after a complete life from serving in its military (Vietnam 1968-1973), having a few businesses, raising a family (first one), and seeing every inch of it. By 2010 I felt its future direction was not for me at all
and besides who wants to repeat doing the same thing in one's last chapter.
The trawler I have "Privasea' (#33) I bought 6 years ago from a German fellow that had it at Rio Dulce himself at least 10+ years; he was 84 at the time when he sold it. They cruised a lot the water inside the Barrier Reef (2nd largest in the world) of Belize like many do, since those are perfect waters for smaller crafts to cruise in, especially a Prairie 29 type (not double haul like a catamaran). It is nothing to see at 50-60 boats in the Placencia harbor from Rio Dulce every winter (November-May), then they go back to Rio and some go back 'home' (to the U.S. & Canada). Many however stay fulltime time in Rio Dulce area or during summer (a fine little town like Placencia) and constantly go to Belize waters on & off.
I suspect 'Privasea' was shipped to Belize at some time either to Barrio, Guatemala or Mango Creek, Belize, both having great shipping harbors. I never asked the previous owner or why it still had a German registry in the first place. Mango Creek is just across the bay from Placencia by the way. Pre-registering before coming is the way to go and there are many ways to accomplish anything in these parts, unlike more formal societies like the U.S. or Canada.
I cruise a lot all the barrier waters north of Placencia all the way to Caye Caulker with mine, in fact it is parked right now 20 miles north of Placencia as I leave it for weeks at a time out of town and use it as a base for local fishing areas. Then travel tom it back and forth with a 25ft. because I live in Plkacencia. I am into flats fly-fishing and use a paddle board to comb the shallow flats out of it.
I highly recommend shipping the boat, after experiencing the Cuba-Cancun passage twice in a 48ft & 54ft single-haul boats not at the best of times and with crazy captains. Being 29ft and about 15k pounds it is really not that much money, I think.
Perhaps flying and visiting Placencia and Rio Dulce area will be a fun and informative trip before hand and deciding which way to go. You are most welcomed to visiting us in Placencia and we be happy to enlighten you the best ways to go about customs, living in these parts, etc etc. We have done such a favor for many folks over the years from NA and even Europe.
Flying back to the U.S. (especially Florida) is a breeze from either place, my whole family including my 102-year old mother and all my sisters are in DeLand, Florida. My 2nd wife (of 13 years) 'needs' to shop in the U.S. every so often (rolls eyes). My slightly older sister (interior decorator) and my wife carry alone like true sisters, and now Belize is my sister's second home; she comes every 2 months. Go figure how life turns out sometimes.
I congratulate you on your mentality, it is understandable. An adventurer's life shouldn't be over when one is 75, on the contrary. We are not alone, there are many of us still.
Trust the above is helpful and what you are thinking is not only doable but makes a lot of sense.