Jim had taken his family
cruising in Canada
in his Catalina
22 trailer sailer, long before he met me. He and I were both divorced when we met, him, with a daughter in college, me with kids
not yet ready to leave the nest. We met crewing
on a mutual friend's boat.
Our process for leaving to go cruising took quite a long time, we met in '79 and did not leave until '86, the first time. We sailed weekends, and summer vacations, and then, by the time we were a "couple", we took a long vacation
together (I had to take time off without pay), and sailed his 30 footer to Hawaii
and return to SF. The purpose of that voyage was to determine if we liked ocean passages, because Jim had the dream of sailing his own boat to French Polynesia
After that voyage, he bought the boat which was to become our first "Insatiable", a PJ 36. We eventually lived aboard and cruised her for 18 yrs.
For me, it was all a process. First, I started sailing, then he and I sailed together, and then he took a sabbatical, and I quit my job, and we left for a year, to find that our financial ducks required more lining up. We returned from Fr. Polynesia to the States, and worked for another year, and I sold my house for the cruising kitty. We got married after we came back to the States, as well. We have been cruising now for about 30 years. We do not plan to re-enter the job market, but if something happened that wiped out our savings, well, I've seen old women in jobs, and I would rather work than not, if I were in need.
What is hard to imagine when you're first contemplating cruising is that eventually you will either move on to something else that draws you to it, or cruise until you can't any more. There is incredible freedom in this life style. It does come at a cost, though, and one of them is less intimacy with family
and other loved ones. If someone is 32 and has no dependents, if he wants a life partner, perhaps he'd meet her [or him] cruising.....
What doesn't often work too well is the wait until 65 and then start cruising: it's a really big ask of a partner who has never sailed, who knows the fallibility of her partner, to give up everything she has worked for to go sailing. It is no big surprise that there are a number of "water soluble" romances, marriages that fail following an uncomfortable passage
...but maybe the marriages were not so strong, any more, hard to know from a distance.
Mike picked up on the acceptable risk issue from the "do go cruising" perspective; and A64 is very interesting here, because his greater risk came from staying in his job, which had changed to become intolerable. And now, he is on the path to freedom. The choice of leaving the society that nurtured you is in some ways anti-social, and is not well received by the ones who do not do it. They seem to think it is a "phase" you're going through, rather than the choice of a different path through life. It's a little like the first time you go off the high dive, you don't know in advance if you'll do a belly flop or a gorgeous swan dive, or something else altogether! But all the guys who've gone off the high dive, they're waiting to welcome you, only you don't know that yet.
PS. Sorry this is so long. I wish I had Boatie's gift for succinct.