You want to know what some of us geezers think about going cruising early. I cannot say that I have a strong opinion one way or another, because going cruising is such a personal experience. For what it is worth, I can only tell you about my own experiences and life.
A lot of us who are approaching geezerhood, went cruising when we were younger, before beginning our 'real' lives. In my case when I got out of college, I bought an old wooden 25 foot Folkboat for $400 fixed her up and lived aboard for a while. I did not have the money, or the urge to do anything more than coastal cruising, picking up odd jobs, parking cars and bussing tables as I went. I frankly I personally find being offshore pretty boring and prefer poking around, exploring places along the coast.
I have owned cruising boats or racer-cruiser type boats of one kind or another ever since the early 1970's, and have cruised for 42 of my 55 years. I still actively race my boat single and double handed, race other people's boats and cruise mostly my own boat. As my sailmaker says, I cruise like most people race, keeping the boat up to speed and shunning use of the engine.
In any event, when I was in my 20's, wherever you looked there were young people out cruising. Most of us were in 30 foot or less, old wooden boats. We lived simply and cheaply. We anchored out in free public anchorages, and used free public dinghy docks. We'd haul out at DIY yards and do our own maintenance. We'd barter and trade stuff, help each other out. It was almost a floating extention of the hippie culture of that era. We'd work for a while, lay in a supply of generic can goods and then keep moving. While I mostly stayed around southern Florida, the Hippie sailors of the 1960's and 1970's went all over the place.
It was a good life but wasn't a full enough life for me. Speaking only for myself, and not trying to imply that one course in life is more proper than another, as a kid I the cruising life felt superficial, self indulgent, and detatched from the world. I wanted to do more with my life than simply sail and work odd jobs.
I eventually went back to graduate school and became an architect. For me there was a lot that I like about being part of a shore based community. And for me I like the idea of designing buildings that will positively touch people's lives long after I am gone. For me cruising was an important part of life but was not the meaning of life. But as I said above that is just me.....I still enjoy cruising and as a long term goal, hope to cruise longer periods of time, eventually retiring aboard and perhaps exploring Europe using my boat as a base of operation.
I get a lot of email from people, of all ages, thinking of doing what you are considering doing. They come from all walks of life and have all kinds of asperations from setting somekind of rounding record, to stopping almost everywhere along the way. They have all kinds of budgets and all kinds of skill levels. The one thing that keeps hitting me is that back in the 1970's, when people went cruising it was in small, reasonably well suited designs.
Today I see a lot more people, like yourself, buying increasingly large, often poorly suited boats (both in terms of build quality and design) and somehow trying to make it work. For examples boats like the Newport 41 were never meant for the kind of abuse that a circumnavigation implies. The Newports were cheaply built, ill-handling, miserable seaboats intended raced by large crews. They can be adapted for offshore work, but they never were particularly robust and I question how well one of these old girls will hold up to the abuse that you intend her to withstand. On the other hand you can buy them cheaply, and the Newport does not make the whole trip, you can always replace like they did with Dove. As the old southern expression says, No great loss, you were looking for a boat when you bought her.
As I track these people's paths, I find that the vast majority, alter their plans along the way. taking different routes, discovering that offshore work does not thrill them, shortening trips or extending trips. Wearing out and replacing boats (sometimes bigger, sometimes smaller) Some spend the rest of their days out there. Some never become distance voyagers.
I don't see this as a failure in any way. To me cruising is about the experiences that youy have out there and there is no yardstick for a successful voyage except getting out alive and mostly uninjured, and truly seeing and feeling the world that passes along the way. It is about getting out there and doing.
With all due respect to Surfesq, I strongly disagree with his position that "This site is for Geezers and Preeners. (Wannabes)." Surfesq has posted his own definition of what a 'sailor' and that definition seems to be quite specific. While it may be valid for Surfesq to define himself as a sailor, I strongly disagree that his definition should be viewed as a universal truth (I am not sure that Surfesq means to do that).
From my perspective, we all come to sailing for our own reasons, and take from it what we want. Stereotypical ideas and grandious plans do not a sailor make. If cruising around the world is what floats your boat, then I think that is quite valid for you to do. But at least around here, I find a lot of people your age who own boats, and sail them quite frequently. To me the joy that they recieve from sailing is no less valid, or no more valid than people who chose to pursue a more aggressive sailing life. That does not make them preeners.There is no universal right and wrong way to be a sailor. There are only people who chose to go out on the water under sail for their own pleasure.