A good question, some important points, and in the “you really have to read this” department…
When looking back, my biggest influences in the sailing world were Robin Graham, Joshua Slocum, Robin Knox-Johnson, Bill Tilman, and the fictional James Troy of “Adventures in Paradise”.
Hey, hey, Gardner McKay…
The thing is, none of the afore-mentioned were yachties. In fact, most of the sailing fraternity I admired were, as it happens…
Just working class folks with boats.
There used to be a pretty wide gulf between YACHTSMEN and cruisers. Yachting has always been a sport or badge of luxury of the monied class while cruising was something altogether different and, being different, was viewed with suspicion. That said, the differences between cruising and yachting tended to keep the two groups mostly apart to the point that a lot of cruisers developed a ghetto mentality.
For instance, yachtsmen had yacht clubs and cruisers did potluck dinners. Quite a difference if you think about it for a minute or two.
Anyway, somewhere along the line something interesting happened; cruising became hip with a capital “H”. Today, aided by heinous cruising rallies and upscale marketing interests, we saw the birth of consumer cruising. Since there was money to be made, it was a downhill slide. Proving the “there’s a sucker born every minute” adage has a lot to do with the marine trades.
Sadly, the new found popularity combined with greed-fueled consumerism is now what cruising is all about. The current dog eat dog and “my condomaran is bigger and more expensive than yours” mindset now passes for the norm.
Of course, if you actually think about it it’s all just a con game. Do your research, avoid the Kool Aid, and ignore the man behind the curtain. It’s still possible to cruise old school.
It’s a big world and you can do it.

I never thought about it, but cruising was definitely a working man’s game, and you could aspire to the boats being sailed. Nowadays lots of cruising boats cost more than a house and are often better fitted out than a house. (How do people afford them) Then the owners have no idea about the stalwarts of cruising like the Hiscocks, Smeetons and Roths who really pioneered the way. I often am reminded by some sailors that if you can’t have a hot shower every night and air conditioning in your cabin then you are just camping. Things have certainly changed and so have the prices. Down Under we have a term “Grotty Yachtie” and they are almost extinct now.
Cheers