Growing up we always did sailing vacations with the fam - but never had a water maker! In the beginning we didn't even have generators or AC. They are amazing vacations, and I think especially amazing for kids. My oldest has gone to the BVI, but my two youngest still haven't had the chance, although they have enjoyed a lot of center console boating in the keys.
Living in a boat takes a certain type. My parents intended to do the great loop this year on their '79 Hatteras 58ft Yachtfish, but soon realized that most of the loopers are boaters, and not yachtsmen. My dad is the type that keeps the boat pristine. Nothing out on deck - tied up a very particular way, stickler for the rules, etc. He has his 200 ton license. He considers himself at yachtsmen. Snobby? Probably... but still. So, they abandoned that idea to just stick with the ICW. They are currently in Maine and will soon work back down to go to the bahamas, and then to Marathan for a few months. I posted it before I think, but here's "Gus" docked in Manchester by the Sea (not a traditional name to be sure). She was there while we fished out of Gloucester for tuna.