It sounds as if you're in love with the idea of escaping somehow to "The Islands", but are not necessarily interested in owning a boat or making a long-term lifestyle change. Nothing wrong with that. Many of us dream daily of white sand beaches, palm trees, and cold Coronas. (Hey, didn't I see that on TV?)
My question to you is why does your escape have to involve a boat? Why not rent a shack on the beach for a few months? Why not settle in there, enroll your kids in school, and get to really experience island life up close and personal? You don't need a sailboat to do this.
I have friends who headed for the islands years ago. They do not own a boat, but hey have rented and worked in Puerto Rico, Aruba, and now live in St. Thomas. They are living the "Island" lifestyle, boat-free.
If you remain committed to the idea of cruising, my advice would be to get charter certified, charter a couple times with your family, and see if you still have the dream. If so, start boat shopping.