I have some friends who have actually circumnavigated the world on their sailboat (the ultimate loop!)- took them about ten years, and they homeschooled their three children. It's been a blast following them, and getting random postcards from places like St Helena and Papua New Guinea.
They run a cool blog here-
https://www.sailingtotem.com/ and make money via coaching people who also want to cruise full time. To hear them tell it, the Bahamas is the place to start because it's easy to reach from the mainland USA (you don't need to do a long passage to get there), and there are a ton of islands close together and it's easy getting supplies/repairs and you meet a ton of other cruisers. Most people apparently who are only cruising for a short period never even get further than the Bahamas for various reasons.
Personally my only issue with the entire thing is to paraphrase Kurt Vonnegut, I am a freshwater person and whenever I swim in an ocean I feel as though I'm swimming in chicken soup.