Originally Posted by thecrabbycaptain
When we say Bahamas, it is just our staring point but we appreciate any suggestions or thoughts you might have.
Don't skip the Bahamas - your plans are good. The Bahamas are a vast cruising ground (they cover 400nm of latitude, and encompass 300-400 islands), and if you spend time getting away from the typical spots, you will find some amazing experiences. Best of all, the cruising ranges from beginner level to advance, so there is a lot of area to hone skills, confidence, and comfort level.
We cruised the Bahamas when we started out, then spent the next 6 years exploring the Caribbean - Eastern, South America, Central America, and all the islands and countries in between. We still yearned for a bit more of the Bahamas, so we came back for a couple of seasons before heading off to other places again. You won't find water like the Bahamas anywhere else in the world, and the fishing, lobster, and conch is so easy.
We hated the Eastern Caribbean, with the French islands being an exception (fantastic cheap wine and food). Just wasn't our style - crowded, full of vacationing charter boats, very little actual culture left, crappy reefs and fishing, etc. It is easy sailing and cruising, and if you need stuff, it is available.
We love South and Central America (except Venezuela and mainland Honduras). More demanding cruising - not as well charted, need to learn Spanish, not a lot of facilities and parts - but a much richer cultural experience, and more undisturbed and vaster nature.