My wife and I dream/plan of doing the same when I retire (5+ yrs out). She also has little sailing experience (a few 1 week charters) but I think she'll be willing to give it a try if we get a large comfortable boat
Can I ask, did you think of getting a cat? I live in Michigan and the GL marinas
are not well suited for cats but my wife prefers them and I'm beginning to as well. Ultimately we will end up in the Carib.
Enjoy the trip,