Sail ever more simply and efficiently: interview with Webb Chiles

Webb Chiles is an American sailor, 5 times circumnavigator and author of seven books. He had throughout his life reached impressive sailing achievements but also, as a writer, he confronted the reader with the fascination of his peculiar human experience, or as his website states he goes “to the edges of the human experience and sends back reports

Webb sailing Gannet- courtesy of

Webb sailing Gannet

Chiles’ website, , is a very complete source of informations about his sailing career and life, his Journals, videos, and much more.

In this interview I am trying to get from Webb Chiles, now half way in the attempt of his sixth circumnavigation, part of this mental experience, if there are fears or emotions connected to it, the inner world that surrounds the physical hard labor of sailing.

I called him on the phone while he was in Evanston, IL a suburb of Chicago, visiting his wife, recovering from 9,000 miles of sailing on his boat Gannet, a Moore 24, and preparing to go back to it to complete his voyage.

FB: Where did the inspiration come from when you first set sail?

WC: The first words of my first book, Storm Passage, are that I was born for it and I think that’s true. In terms of how this all began, I was the only child in my family, I have no brothers and sisters and I wasn’t close to my mother or my stepfather so I spent a lot of time alone, even if they were in the same house with me. I was in St.Louis Missouri, in the Midwest far from the ocean. As long as I remember I always wanted to be a writer and I always wanted to sail the world and I managed to combine the two. The writing part was something I’ve always done and I still do.  I can’t imagine not writing. I wrote for 20 years before being published, which is not an uncommon situation. I read Slocum in particular that gave me some inspiration, but I usually don’t make other people into heroes that I want to emulate.

My grandparents, my father’s mother and her last husband moved to California in a little house near the beach and I spent my summers with them and saw the boats sailing and I said someday I’m going to do that and I did. Being an only child I was used to be alone so I have mostly sailed alone. Being alone is probably an essential fact of our species, which is odd because we are herd animals, but each somehow knows that he or she are alone inside the herd. For me that was my common experience

FB: It’s a sort of paradox. Society doesn’t really encourage this type of behavior. Going sailing alone is not a very productive way of life but at the same time Society celebrates explorers, and sailors and people who push the limits. How do you live this contradiction? 

WC: I named my very first boat Egregious. In English that now means something that is flagrantly bad, but when you look at the etymology of the word it used to mean something that was outstandingly good. The Latin roots of it E- meaning “out of” and grex, gregis that means “herd”. So Egregious means originally “out of the herd”. Since the rise of democracy to be out of the herd is considered bad, before democracy being out of the herd was considered good. Both meanings applied to that boat, but I physically was sailing away. That was my first voyage, a two stop circumnavigation via Cape Horn, and I was continuously at sea for 5 months at one time, so I was certainly away from the herd, and often I had been since, so that’s why I called the boat Egregious.

FB: You obviously crossed oceans many times, on an open boat sometimes, on ultralight fiberglass shell like Gannet, so you must have a very particular fear threshold. How would you deal with fear of the ocean when you take a small boat out?

WC: People often say I am brave, but I’ve never said I am brave. What I think I have is nerve, which is not the same thing. Being brave or being courageous is doing something you are afraid to do and I don’t do anything that I’m afraid to do.  Nerve is different.When you prepare to do something, whether it’s sailing a boat across the ocean or climbing a mountain or doing anything that has an element of danger, you prepare yourself and your equipment as well as you possibly can given your resources. Having nerve is the willingness after you’ve done all your preparation to embark upon something whose outcome is uncertain and may be fatal.

I’m not afraid to be out there by myself on a small boat, the biggest boat I had was 37 feet log, not a big boat by any means. Gannet is 24 feet, ultra-light and small, a very small 24-foot boat. Chidiock Tichborne, the open boat, was of course even smaller. Most people are afraid of the unfamiliar, I’ve spent nine or ten years of my life alone doing passages. I did write about fear in Storm Passage but that was when the ocean was more unknown to me. Of course the animal feels fear when something unexpected happens, such as when suddenly you’re out of control when a wave hits the boat and picks it up and throws it sideways, and the animal inside you naturally reacts to that, but that’s very quick and transient. At this point, I survived capsizing three boats, putting the masthead in the water (Egregious’ went in the water two or three times) Gannet had the masthead in the water this year. I also have been in Force 12 (hurricane force winds) at least 8 times. When you have the knowledge that you survived those things you are not dealing with an unfamiliar element anymore. We do fear remembered pain. My greatest fear about Gannet is that it will turn into a survival ordeal that will be as painful as when I was adrift in Chidiock Tichborne for 2 weeks after it capsized, or  the 26 hours that I swam after Resurgam sank.  In both of those cases the greatest pain was thirst. Thirst is terrible, and so my fear in Gannet is that something will happen that will turn it into a survival situation like that and I will have to suffer as I suffered in the past, but that is not constantly on my mind when I am out on the boat.

FB: What are the emotions you feel out there? How is your mental mood? Can you describe a little bit how is your internal state when you’re sailing?

WC: I was long ago a philosophy major and perhaps because of that I am not a mystical person. I like to think I have the brain of a scientist, the body of an athlete and the soul of a poet. I do not hallucinate or hear voices at sea, though I did once or twice on my first circumnavigation. To me being out there is natural.

I was reading a book recently about survivors of extreme situations.  I have been in survival situation three times. For five months on  Egregious from San Diego around the Horn east to New Zealand. The hull was cracked for most of that time and I was bailing 7 tons of water every 24 hours with a bucket to stay alive.  This is all related in Storm Passage. The two weeks I was in the inflatable after Chidiock capsized in the Pacific in 1980, and then the 26 hours when I swam and was carried by the Gulf Stream for 125 miles after Resurgam sunk.

I learned from that book that even among extreme survivors I am atypical. In most of the stories the survivors heard voices or a voice that spoke to them, and I have not. Most of them prayed.  I do not. I was raised as a Presbyterian, but studying philosophy cured me of that. The third thing that most of the survivors had was someone to survive for, they kept themselves alive for someone they loved, and in two of the three of my survival situation I had no one to survive for. When Chidiock was adrift I was with Susanne and I did think of her and wanted to survive for her, but the other two there was no significant other in my life.

When I go on an ocean passage I say I am entering the “monastery of the sea” and I love doing that. There are contradictions in all of our personalities.  For those who know me, I am the person who has spent the most time totally alone—I’ve been at sea for a total of eight or nine years–and I’m also the person who has married the most. I like having a woman in my life.  In the monastery of the sea, I’m a much married monk.

I love it out there. I love the purity of it.  There is great beauty. I am not by nature an urban creature anymore.  I don’t like cities.  They are ugly and noisy and cluttered. I love the purity of being out there.  There’s no ugliness out there.  There are no sounds except natural sounds or whatever music I choose to play.

Although Gannet sails very well, she is also very wet and her motion is very quick, so even though I don’t get seasick, every little task is difficult to do. I was 55 days non stop between Darwin and Durban.  As you may know these boats are still sailed singlehanded from California to Hawaii but nobody has ever sailed one further than that, except me. They are tiring to sail. I am an old man, but I’m still in good shape, so I don’t take age as an excuse.

FB: Are there outdoor environments other than the ocean that you like to be in?

WC: I am a specialist in this sense.  I know that mountains, the desert, even polar regions have the same attraction to some that the ocean does to me, but I like to think that I do a few things really well. I think I sail well, I write well and I love well. I always liked simplicity and instead of doing a lot of things, I just do those that I can do well and stick to them.  When I’m sailing I sail and when I’m here, being with my wife Carol is my highest priority. I also buy stuff and prepare to go back to Gannet.  A lot of things are much easier to buy here in the United States. It may or may not still be a great country but it’s still a very efficient marketplace. So when I am not sailing I don’t participate in other sports. I concentrate on different parts of my life and try to keep it very simple.

FB: I was just reading a novel by Conrad, Chance, in which one of the characters particularly despises life on land because he says that people on land work half as much as people on boats, and therefore they become lazy and soft compared to seamen. How do you feel about the separation between sailing life vs. land life?

WC: For me it’s kind of like moving between the war zone and being on R&R. When I’m back here I still work out, and try to stay in shape, but I also rest. I like to use my body. Unless you’re struck down by a illness, if you don’t use your body you’re definitely going to lose it, so I have my disciplines. The fact that life is easy on land is part of recovering from when every action was very difficult while sailing. After doing 9000 miles on Gannet I was very glad not to have to do anymore for a while. Next year I may have to do 11,000 miles all the way back to San Diego, although I don’t know if the timing will work so I can get there before the hurricane season starts on the West Coast of Mexico.

Perhaps the average man sits around and drinks beer and watches television when he’s not on the job, but it seems to me that there is more to live than that.

Webb aboard Gannet

Webb aboard Gannet

FB: Do you feel a connection with the boats you owned and sailed? You certainly had very different boats in your life. Do you ever think back to your previous boats or you just focus on the boat you have at the moment?

WC: I am on the record saying I don’t love boats because I refuse to love anything that won’t love me back, but I have a great affection for some boats, particularly small ones, because small boats do so much more than most people expect they can. I’ve only owned seven boats and did my major voyages on five boats, starting with Egregious which was an Ericson 37. Chidiock Tichborne, a 18 ft Drascombe Lugger open boat . Then Resurgam an English built SHE 36 designed by Sparkman & Stephens.  Then the Hawke of Tuonela which was another 37 footer.  And now Gannet, a Moore 24. Egregious and Hawke of Tuonela  were both IOR 1 tonners, Resurgam was a 3/4 tonner.


the Open Boat – Chidiock Tichborne

Of these, three were great boats. Resurgam was just right at sea.  One of the limitations of how fast my boats go is how well self steering vanes can steer them to their full potential. I actually went faster with Resurgam  than the two 37’s because she was so well designed that the self steering could control her close to 100%.

I have great affection for small boats. With Gannet one of the most interesting parts has been solving how to live in her tiny cabin. I have to sit on the floor boards to sit up straight.  The beam is only 7’2”. I can almost reach from side to side.  The important parts of my life are sailing, writing, listening to music, reading, and Carol and I can fit all them on Gannet, except Carol, and Carol doesn’t want to fit on Gannet anyway. She does not like Gannet, which she finds is too small and quick and wet.

Gannet may be my last boat, and she, too, is a great boat and I’m looking forward to getting back to her.

FB: What’s your writing routine on passage? Do you take notes anytime or is it weather dependent? 

WC: As I have said Gannet is very wet.  Even with the companionway closed, a lot of water still comes in, and everything gets wet inside.  If it can be damaged by water then it has to be protected. Not all protection is equal. I have had a lot of waterproof bags that proved not to be waterproof. I do have very good Pelican boxes which really are waterproof for my laptop, iPhone and my iPad Mini. Most of the times I write my passage log on my laptop, but there are times when I can’t do that because too much water is coming in. When that’s the case I have some notebooks with special paper you can write on even when it is wet, so sometimes I make notes in pencil, otherwise most of it goes into the laptop. Each noon I record my daily run from the previous noon, speed and course, position, and when I make other entries into the passage log depends on what’s happening. There’s no specific time that I write other than at noon, and sometimes I just write down a few words to remind me for when I can use the laptop later.

For many years now everything that I publish has been based on my passage logs. My journal has been online for 10 years now. Of course I kept journals for long before there was an Internet. I think blog is an ugly word. I prefer Journal and I keep one partially for memory, partially as a basis for what I am going to write later.

When I get into port and I write an article, the routine is different. I write first drafts almost first thing in the morning. I’m a morning person and before I have to deal with the world and can be distracted I usually write 300 to 400 words and then stop, even sometimes in mid-sentence because that is a good place to pick up the next day. I work at first drafts every day, 7 days a week for however long it takes. I don’t break that routine unless it’s really unavoidable Once I’ve done those 300 to 400 words ,I can go about my day. I don’t particularly think about what I’m going to write next, at least not consciously. I enjoy rewriting more than writing a first draft. I can rewrite any time of the day, and I keep rewriting until I get to the point where one day I’m just changing back something I changed the day before and then I know I am finished . You can rewrite forever and finally just have to stop.

FB: How do you do with books onboard?

WC: I am a totally converted e-reader. I do not read paper anymore except in rare cases where I come across something that I want to read and it isn’t available as eBook.

Gannet of course has no room for books and they wouldn’t survive in her anyway. I have a Kindle which is a very superior e-reader but I don’t use it on board as it’s one more thing to have to carry halfway around the world, so my e-reader is my iPhone and my iPad Mini. I have more than 300 books in them, including the complete works of Conrad, Twain, Kipling, Zola and many others. Also I have more than 600 albums of music on them.  It is amazing how much we can carry in our pockets.

FB: Are you still learning? What are you learning right now with Gannet?

WC: That’s a very good question and I don’t have a quick answer.

I think that basically we are problem solvers. You pointed out that I have had different kind of boats. The reason for that is that I was seeking new experiences. With Egregious, for example, I did my first circumnavigation during which I became the first American to go alone around the Horn. After that voyage I didn’t want to do the same thing again, I wanted to have a qualitatively different experience and that’s why I went to the open boat, Chidiock Tichborne. After sailing Resurgam and the Hawke of Tuonela, both of which I lived on with the women in my life at that time, with Gannet I again wanted a whole new experience, and it has been. I think I’ve solved most of the problems with her. The learning experience was a pleasure.

This year I went back to sheet to tiller self steering on Gannet, that is all I used on Chidiock  and on Egregious for about 10,000 Miles when her steering vane was torn apart south of Australia in that circumnavigation.

I look forward to the element of uncertainty that is a part of any voyage.  With Gannet the limits and the thresholds when things become difficult and dangerous are lower than they are on bigger boats.

There are many words that have been debased in modern societies and among them is adventure. You find adventure used for something that is really pedestrian mass tourism.  I make a very deliberate effort not to have adventures. I think you should try to make sailing your boat as easy as possible and to make  yourself as strong as possible.  Even so unexpected things are going to happen, and I look forward to that. As I have gotten older there are times that I do wonder whether things would seem less difficult If I were twenty or thirty years younger, but I still look forward to pushing limits, my own and Gannet’s, and the edges of human experience.

In the introduction to my website I say that the defining function of an artist is to go to the edges of human experience and send back reports and I like to think I’m still doing that. I still enjoy that I don’t know what those reports are going to be.

So I’m not sure what I am learning, but I do know that I continue to study how to sail ever more simply and efficiently. I take a profound pleasure whenever I can remove something from Gannet. There is curiosity about sailing an uncertain voyage and seeing how I respond to the unpredictable problems that will inevitably arise.

6 thoughts on “Sail ever more simply and efficiently: interview with Webb Chiles

  1. Bernard Zidar says:

    Great piece Fabio. Sail on, safely.

    1. fabiobrunazzi says:

      Thanks for reading Bernard!

  2. Brian & Deb says:

    Great work, an excellent interview with a fascinating sailor!

    1. fabiobrunazzi says:

      Thanks for enjoying it, Brian and Deb!

  3. Rick Bartley says:

    A very thoughtful interview. Well done, both of you.

    1. fabiobrunazzi says:

      Thanks for reading Rick!

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