I have to confess, my comments on this thread are related to MY and the Admiral's decision to sell our business, our home and move on our boat and sail away. We have gone through all of the "what if's" and "does it make sense". Well there are a lot of "what if's" as there are in life, and it probably doesn't make sense. We spend our lives limiting as much as we can the "what if's" so it goes against our grain to put ourselves in a position of limitless "what if's". But that is the exiting part, life has become a sort of a drudge, in that we have been pretty successful at controlling what comes into our lives and planning for the outcome. Our friends are of mixed opinion's. Some question our "throwing reason to the wind" frame of mind. Other's are exited, because they have come aboard for a week or so sailing with us and now they realize no matter where we are they are welcome aboard. Built in and cheap vacation for them. Our kids are supportive but apprehensive. They question "Dad can you do this". They know me the best. I have gone to school and gotten my Captains license, gone to diesel mechanics school to relieve them of their apprehension. Now they are exited to visit. We own a large heated storage unit so there is no problem with storing some of our important land processions for what reason I don't know other than we have things that were passed down to us from my parents and grandparents and great grandparents that will pass on down to my kids. So I can't divest myself of those things.
When I looked at retirement, I didn't think I would ever retire, I am a work-a-holic and loved what I did, so I didn't see retirement in my future. Now I do, living and cruising on our boat is a full time job. Our goal is long range, Mexico, Caribbean and South America is in our future. Why because we "bare boated" in those regions and experienced them and love it.
We have worked hard to become financially able to do this, my granddaughter has her real estate license and is going to manage our rental properties. She has volunteered to go to our post office box and get our mail once a week and scan to us the important things. So we are ready to do this until we are physically unable to do it any longer. Then we will kick one of our renters out and move into one of our rentals. Have we missed anything? I think not. I have no regrets, only a great anticipation to this January when we will physically move from land to the water.
Our decision on a boat is one that can go anywhere in the world and the biggest we could afford. We did not want to buy a less expensive boat and refit it, we bought the biggest boat we could afford that had everything we needed to cruise where we wanted to go and beyond.
It is interesting to read the other comments and views. It seems there are people that use their boats for second homes, others are marina dwellers mostly, and a few cruisers, but it seems like there are fewer of the later in this thread. It makes no difference who you are, and your reasons, you are on the water and that is where I have found the most peace, experiencing the moods of the water while on a boat and being influenced by it. I feel the most alive when there and that is where I have chosen to live out the rest of my life whether it makes sense or not, it's a life choice.
Is this for everyone? NO! I have friends that would never survive. One close friend went with us for the year and a half we spent looking at boats and went as a potential buyer also. The plan was for both of us to buy boats and cruise together. They backed out and bought a condo in Palm Desert CA. on a golf course. They discovered it just wasn't them. The condo on the golf course was more their style. But they love to visit the boat for a week or so. Another friend and his wife moved on a boat after a while she moved back on land, he stayed on the boat. So goes life. So I guess if you are not suited for the boating lifestyle you will have regrets and move back to land. So the most important question is to look introspective at yourself and ask, "is this me?". Can I be happy on the water in a boat? Trading friends, family and the comforts of a land based house for a small in comparison boat and what comes with it. It seems like most of the maintenance falls on me and I have tinkered with mechanical things all my life. My boat has so many different systems that need constant maintenance it will keep me busy, which I need to be. So it works. And by the way my wife is anxious to learn so while I do maintenance she is there learning. So again you need to go through the retrospective phase asking yourself the hard questions and as a couple, can you live 24/7 with each other in a relative small space sometimes under stress (weather, system breakdowns, meeting new people, never in one place etc.). it's up to you to know yourself and as a couple. The only way to know "if there will be any regrets". Someone famous said "know thyself..."