The Myth of the Sailing Elite

Charlie Deist
2 min readMar 17, 2022

People think sailing is just for rich people.

You know the stereotype: yacht clubs, salmon shorts, topsiders, and a polished sloop. When something breaks, the owner Breaks Out Another Thousand, and pays someone to fix it. You might think that if you’re not born into sailing elite, you’ll never get out on the water.

But it doesn’t have to be this way.

Anyone can sail.

I never stepped foot on a sailboat until my twenties, and now I’m a licensed captain with a charter business, and I teach sailing on the side.

It all started with a desire to learn, and a willingness to ask for help. I tooled around at the Cal Sailing Club until I got an intro to dinghies. I sailed on friends’ boats. I talked to the crusty guys on the dock, and let them show me how to rig my boat when it was obvious that I was in over my head.

If I believed I would need to spend a ton of money to continue my hobby, I never would have tried to learn in the first place.

Put feelers out to the right communities, and you will get a bonafide sailing education.

As with anything, it starts with a serious intention.

Then, you find out where the sailors hang out in your area — outside the fancy yacht clubs. Usually, there are loads of people of all levels of expertise looking for crew for racing or just cruising around.

Here are three ways to accelerate your learning:

Tip #1: Find out when race day is and show up with a six-pack of beer. So-called “beer can races” are not as fancy as the big regattas, and the better the beer, the faster the boat you’ll get on (usually).

Tip #2: Join a small boat club. Start with dinghies to get a feel for the basic terminology, points of sail, and mechanics of a sailboat. This will give you a preparation for tip #3…

Tip #3: Buy a cheap (but not free) boat. Look for something in the 15–25 ft range, with a solid outboard and set of sails. Nothing fancy, but not a project.

If you continue to think sailing is out of reach, it will remain so.

Don’t let the rich dudes in the pink shorts have all the fun.

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