Welcome aboard SP.
Since you say "move the boat", what do you have? Are both you and your wife experienced sailors and have you lived aboard for any length of time before?
It's a bit hard to say that you will like to "live out the rest of our lives" in the Caribbean, if you "know nothing about the area".
It's beautiful for sure, but its huge and diverse. There are big differences and costs from one island to the next and, except any territory of your native country, you will have to deal with and pay for visitors visas.
Is it feasible? Sure.
Realistic? Depends on a lot of stuff you haven't revealed yet. We look forward to hearing more.
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In the harsh marine environment, something is always in need of repair. Margaritas fix everything.