who used to be in the same biz as me (we were competitors and still keep in touch) is doing exactly that.
He and his family are buying a 50ish foot cat sailboat and moving aboard. They're going to homeschool the kids and live in the Carribbean, complete with compressor and such.
Sounds like fun to me.
I can't get my arms around taking my daughter away from the social interaction with her peers, or I'd have considered the same thing. As it sits I'm happy to be able to get offshore whenever I want, and to tool around in the summer months, at least for now.
I might feel differently about it when she's older, or perhaps not.