Three Steps to Take

By Derek On August 25, 2011 Under Post

There are three basic steps, each harder than the one before and the last one truly the hardest of all. Here are the three steps and we will talk about each:

  1. Learn to sail/handle a boat – pretty obvious, right?
  2. Buy a boat
  3. Go

The third point, Go, is the most important.

Learning to sail

Learning to sail is fun and it is actually rather difficult at first. You need to learn what all “the stuff” on board is called, particularly what the names of all those ropes. Just remember, there are no “ropes” on board a boat; they are “lines.”

If you remember one thing, remember that! It will set you apart from the landlubbers.

(Note: On bigger boats there are two places a “rope” may be found and called as such: the rope that rings the bell used in fog and the rope used as a handhold on a passerelle).

There are a great many good books out there on the subject worth reading and this blog isn’t the place to get into all the detail. However, no matter how much you read you still have to get out there and practice.

Like riding a bicycle, or imagining what chicken tastes like if you have never tried it, you learn by doing.

Or as Confucius said:

“I hear and I forget.

I see and I remember.

I do and I understand.”

There is something really magic about being in a boat on the water when the wind catches her sails and you start to move forward. It is a little thrill that you don’t soon forget and I feel it every time.

As for schools, Colgate School of Sailing  and ASA have good sailing programs you can work your way through. They start at the beginner level (always a good place) and go all the way to “offshore.”

There is probably a sailing school near where you live. If not, you can book a sailing school holiday. Fly to one of the warmer bases for the above mentioned sailing schools, like Florida, take a week off and do it. You will have a blast.

(Note: If you already know how to sail and your partner doesn’t, I don’t recommend trying to teach them yourself. This never works. A better method is to sign him or her up for classes with another instructor. I did this for my wife and she went away on a coastal sailing class for a week without me before we took off on Tehani-li. It was a good confidence builder for her).

Once you get the basics down, and it doesn’t take long, you might want to look into doing an offshore class. There are some terrific ways to do this. Orange Coast College in Newport Beach, California, has long offered well regarded long distance sailing courses.

John and Amanda Neal of Mahina Tiare Expeditions are a husband and wife team with a Hallberg Rassy 46 that run a top shelf operation cruising the S. Pacific (and other places) and have a great website with lots of info too.

Finally, the ultimate must be to voyage on Pelagic with Skip Novak down to the Antarctic Peninsula. Some day I would love to do this. Check out his website.

Buying your boat: Rule #1 (and Rule #2)

You should spend time on as many different boats as possible to see what works and what doesn’t before you commit your own hard cash to buying your own vessel. You will also see what you like and don’t like about each boat you sail on and can apply that knowledge to your future sweetheart.

The number one rule of boats is: “You can have big, fast and cheap. Pick any two.” (The number two rule is the word “Boat” stands for, “Break Out Another Thousand”).

Everybody wants the biggest boat they can afford. It is natural. Bigger, well-designed boats, are also more comfortable at sea. But everything and I mean everything, costs more with a bigger boat. You need twice as much bottom paint (at $100 a bucket?), your lines are 2-3 times longer (at $3 a foot?), you pay your marina by the foot, etc. It continually adds up (rule number two).

The best policy is to buy the boat most suited to the trip you will take. If you are coastal cruising, you do not need an offshore passage maker. If you are cruising, you do not need a composite Open 60 racing sled. If you just want to sit on the boat and drink beer, you can pick just about anything. Famed nautical yarn spinner Tristan Jones has a few words of wisdom on the subject:

“Get what you can afford,
Sail what you can handle,
Love what you’re doing.”

The best website globally for buying and selling boats that I am aware of is: I have been a fan for years and have found my last two boats here. If it isn’t listed on yacht world, it probably isn’t listed. I recommend spending a lot of time on this website changing the parameters of your search and seeing what is out there.

A good idea is to keep an eye on prices around your range for six months or so until you know what things should sell for. I did this each time I was in the market and could look at any boat anywhere in my range and guess within 5-10% what the asking price was. Then I knew I was ready to buy.

Talking to brokers is also a good idea to get a sense of the market in your area. Beware, though, they have an agenda and that is to move boats. Don’t get overwhelmed. If they ask damned annoying questions like, “Are you ready to buy a boat today? Are ya?” Go somewhere else. NOBODY is “ready to buy a boat today.”


Once you buy a boat you will be thrilled and probably won’t be able to sleep. Ask some experienced sailors to go out with you for your first few sails and take time to figure out how everything works.

It may be extreme, but we spent almost six months living on board our last boat, Tehani-li, before taking her out of the marina – just to learn where everything was and what it was for! That was the only way for me to feel confident I would know what to do if anything went wrong.

Every marina is full of dreamers with boats who always think (and talk) about cruising to far off lands but for some reason or another remain forever tied to the dock. They all have their various stories and excuses – and it makes marinas interesting places to hang out. Just remember the old saying,

Men and ships rot in port.”

It’s a big world out there. And there are those who believe you should see it from the deck of your own boat. Nice.

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