Sailing is to the bay area what Aspen is to skiing. If you live there, you just gotta do it. And so, since I live in the bay area, I just had to start sailing.
Now, the traditional approach to start sailing yachts is to take a basic keelboat certification course. This lasts a couple of weekends (4 days) and costs about $500. After that, you can charter small keelboats (about $200 for the day). You can also join a yacht club (a few thousand per year) which will reduce the cost of chartering. Taking additional courses, another $500 here and another $500 there will allow you to charter bigger boats (about $400 for the day).
Skippers who sail frequently are constantly looking for people to serve as crew for their boats. Only special setups allow you to sail your boat single-handedly and even then it is usually an inefficient (for racing purposes) and somewhat risky proposition (for racing boats, less so for full keeled cruisers) compared to having more people on board. Racing boats in particular are generally constructed to require several crew members to act as ballast on the high-side to balance the boat and keep it on its feet.
Crew members who are able to commit to showing up on a consistent basis are highly valued and skippers are generally willing to train such people for free.
Price of admission for a consistent person: Free training and free sailing.
Price of admission for someone who can't find the time: $1500 for the training and $200-400/day.
Okay, it has not been entirely free. I have spent close to $500 in safety gear in the form of an offshore life jacket, a double tether, strobe light, and an emergency rigging knife. I also bought some dinghy boots on clearance ($36 instead of $70). I got some used foul weather pants on ebay. My "foul weather" jacket is actually my winter jacket.
Indeed, someone who is willing to spend frivolously can easily fork over $800-1000 on the latest fashion in foul weather gear (it changes every year). In terms of durability, it's not going to beat standard fisherman's rain gear. In general, then, you can pretty much pay as much as you want. I'm sure the latest outfit from Gill would make me look snazzy but it's not really going to earn me any respect on the water, so why do it?
Anyway, that money has been paid. Henceforward, my cost is pretty much time, not dollars.
I realize that since I no longer spend any money of any significance on this, my standard of living has dropped. Yeah, that was a joke, and it would be funny if some people actually did not believe that spending very little automatically means not really living life.
In terms of living life. Well, what is living? Living to me is learning. Learning about myself and the rest of the universe. (To some it is experiencing things. To others it is fitting into the traditional structures of society.). Learning happens the fastest when boundaries are pushed. This is the only way to experience something which is fundamentally different.
Experiencing self-similar situations a hundred times over is really only one experience. I have traveled to 14 countries, but they all pretty much followed the same "traveling to a foreign country"-recipe. Anyway …
During my short tenure of sailing, I have experienced [not all at the same time, fortunately] force 6 winds (that's when they put out a small craft advisory), 10 feet waves (they make you feel really small), being on a holed/(slowly) sinking ship, ripped head sail, ripped mainsail, more broaches than I can count, losing the rudder, losing the engine, losing the radio, losing the bilge pump (automatic and manual), rescuing another boat by pulling it off a lee shore, … and a whole bunch of other less dramatic stuff (seals, dolphins, sea lions).
[I have learned how I deal with fear, anxiety, and how I respond to scary situations. I think I take a more relaxed attitude to physical danger now. And then of course I learned a bunch of technical stuff about sail twist, the slot, the foot, the belly, etc.]
I realize that it's the crazy stuff that makes for the best stories but I have also been on the boat finding a finger of air sailing in the haze with the fog whisking around the sails while the sun was setting over the water and the boat was gliding along at 4 knots. Or sailing parallel to the waterfront feeling the breeze and watching the lights of the city and the navigational lights of the other ships. Beautiful stuff.
Yes, yes, I know. I'm not spending money. Consequently, my life sucks, right?
In a little over half a year, I have sailed about 40 times. That's probably more than your average boat owner or keelboat certified boat charterer gets to sail in 5 years or so. Does that mean I'm living 10 times as fast as the average person?
What is the difference between paying and nonpaying?
The paying person does not contribute much value to system. He extracts value. Therefore he pays money. Conversely, the nonpaying person provides value. Therefore he does not pay.
I'm usually in charge of trimming the mainsail. The mainsail trimmer is the person most directly responsible for making the boat go fast—or at least he's the one receiving the majority of the blame if the boat is slow. To provide more value (and because I want to improve my skills) I am therefore spending time studying trimming and rig tuning and what have you. I am not an advanced trimmer, but I am not a beginner either anymore. In particular, I am not a nonsailor. I am not trying to brag here, but rather trying to explain the differences: A nonsailor will pay for the ride either with money or by asking very very very nicely (maybe you know a boatowner). A person willing to commit to a crew position will get onboard for free and be trained. However, this will only happen if a more advanced person is not already available. You see, skill provides value. (This value is in short supply which is why there are occasional openings for rookies.)
If we transplant this to other areas of live it begins to make sense how it is possible to have a high quality of life yet spend very little. You do not necessarily have to provide the value to others. You could also provide it to your family or just yourself.
If you can't provide value. Then you pay. In which case, ironically, you're perceived to have a high standard of living.
It boggles the mind.
Of course people may argue that gaining the skill is work. I don't really see it that way. I am naturally inclined to try to improve myself in matters that I find interesting. That's what humans do. They play music, not because they hope to be famous, but simply because they like to improve or because they just enjoy it. At one point, however, they will be good enough that they will provide value to others which will result in all kinds of benefits. This happens if a person has enough time for practice. Without the practice, a person must pay.
This is the essential difference between a consumer and a producer. (More details in the book about that.)