No plan is fool proof. Not having a plan is a good way to turn a big fortune into a small one in short order. A little money helps but a fortune is not necessary, provided you have a plan.
I knew an old geezer in Honolulu. I don't know how old he was but his license plate said "Pearl Harbor Survivor". Thjs guy had really been around. He lived a board a CT 41, I think, and used a walker to get out to the parking lot where he kept his Lamborghini Diablo. He had traded his viper in on it. Both cars were red, of course. When he ultimately reached the point where he could not get on and off the boat by himself, he got a condo overlooking the marina. The man had style, and that is the point.
I am of the opinion that if you can afford to sit in a marina, you can certainly afford to go cruising. But if you are physically unable to go cruising, or simply tired of it (Yes, people do get tired of it), then what?
Several people have posted here that they plan to go off on a world cruise then return to work. Does that mean sell the house to buy the boat and cruise, then sell the boat for a down stroke on a new house and continue with normal life? Several have said that they want to retire and go cruising. Does that mean sell everything and sail off into the sunset until you die? Some want to live aboard while they maintain an otherwise normal life. We think life is a journey and cruising is just a part of it. Therefore, it is only prudent to plan for the next phase.
I knew a lady named Audrey Sutherland who wrote a couple of books and became a sort of guru among the kayaking geeks in Hawaii. The thing that made a lasting impression on me about Audrey was that she wrote that at the age of forty or so she realized that she needed to prioritize the things she wanted to accomplish in life, placing the physical stuff first - swimming the north coast of Molokai, kayaking southeastern Alaska, followed by the more intellectual stuff like teaching, writing, etc.
We know that we will not be able to do what we are doing now forever. We have had to give up some physically demanding things in the past; soldiering, motorcycle racing etc., besides, we have other things we want to do before the dirt nap. We are not rich, but we started fifteen years ago setting up the "Next Great Adventure". Everyone has their own dreams. Ours involve Morgan horses, maple sugar, brown trout and a vegetable garden. We call it "Starlight Farm". Forty acres on the Missisquoi River that we paid less than the cost of a new car for twelve years ago.
Maybe we'll build a dock and float Lealea in the half acre pond in the pasture.