An Artist of Words, Wind and Women

"I’ve made my voyages to please and interest myself.  I’m glad that others read what I write; but I would have sailed as I have if no one else ever knew." - Webb Chiles

I created this website,, to document my own growth as a sailor. Remembering where I came from and how I acquired a certain skill or memory is important to me and I've found is also sometimes of interest to others. A lot of the content on the website is my way of exploring the sailing lifestyle and examining the many different perspectives that make it so fascinating. 

From time to time, I've brought in experienced voices to help me sort things out. For example, both Ted Brewer and Bob Perry have generously written guest posts here about bluewater sailboat design. In this particular post, I'm excited to share an interview I recently did with Webb Chiles, a well-known enigmatic sailing voyager who's completed 5 circumnavigations in a variety of sailboats spanning several decades.

If you've been reading my blog and have an interest in ocean voyaging aboard a sailboat, I'd be shocked if you haven't already heard of Webb Chiles. In all likelihood, many of you have probably read one or more of Webb's books, several of which are available through Amazon in print and/or Kindle format. I particularly enjoyed The Open Boat, which chronicles Webb's epic 7,000 mile voyage alone across the Pacific in an engineless 18' open yawl.

Webb holds sailing knowledge and perspective that would take most people several lifetimes to amass. Consider just a few of his experiences that we can all learn something from: five circumnavigations, first American to sail alone around Cape Horn, the sinking of his own 36' sloop and subsequent 26 hours of floating and swimming to survive, and the braking of Sir Francis Chichester’s record for the fastest solo circumnavigation in a monohull by more than three weeks. Even at his current age of over 70 years old, Webb still hasn't written his final chapter. He's planning a 6th circumnavigation on another small and unassuming sailboat.

I've read a lot of Webb's articles and books and I've heard him interviewed, but I still had questions. Fortunately, Webb was gracious enough to give me a bit of his time for an interview while he's wrapping up his preparations for the 6th circumnavigation attempt mentioned above. Read his answers below.

An Interview with Webb Chiles, by Kevin Walters from

Kevin (SFLF): Why do you care about sailing and going to sea?

Webb: The best answers I can provide to some of these questions are found on two pages of The introduction and The credo, which was originally a short magazine article.

I can’t do better than that.

Kevin (SFLF): What would you say to someone contemplating a major decision to give up a 9 to 5 career and a secure life on land for the uncertainties of cruising the world by sailboat?

Webb: I neither encourage nor discourage, but give the benefit of my experience when asked without claiming that my way is the only way or the right way.

But in considering your question, it occurs to me that if someone needs much outside encouragement to leave what appears to be a secure life ashore, probably they shouldn’t because that encouragement won’t be there offshore.  The reasons to go need to come from within. 

Kevin (SFLF): I often hear people who are considering a major sailing voyage repeat Lin and Larry Pardey’s advice of “go simple, go small, go now”.  What do you think about that advice?

Webb: I don’t believe the Pardey’s have a copyright on that advice.  I love small, simple boats.  CHIDIOCK TICHBORNE, my 18’ open yawl, was about as small and simple as they get; and GANNET, my present boat, an ultra-light Moore 24, is probably among the smallest and simplest boats presently being prepared for ocean voyaging. 

Chidiock Tichborne. Does she look like an ocean voyager to you?

However, I don’t see many people going small and simple.  Over the years the trend has been just the opposite.  Forty years ago the 37’ EGREGIOUS was average size in the harbors of the world.  On my last circumnavigation in 2008-09, the 37’ THE HAWKE OF TUONELA was usually the smallest or one of the smallest boats in sight.

One of my greatest satisfactions in preparing GANNET has been figuring out how to live on her.  I now can and do everything important to me, write, listen to music, read, sail, except be with Carol, my wife.   But the fact is that few people really want simplicity.  Most want to have everything they have ashore on their boats, and pay the price in complexity, expense and delays for repairs and parts.

Kevin (SFLF): You once wrote in one of your books that the hardest part of fulfilling a voyaging dream is returning to land and all of the emotional, physical and perhaps financial bills. Is there a way to prepare yourself for those realities? Does sailing offer you an escape from those 3 types of bills?

Webb: I must admit that I have forgotten writing that.  It must have been true after my first circumnavigation, but has long since ceased to be for me.  Even though I’ve spent time ashore and as I write this am in Evanston, Illinois, from the time I left San Diego in 1978 on CHIDIOCK TICHBORNE at the start of my second circumnavigation, I’ve never really come back and reentered society.  There has always been a voyage ahead.  There is nothing ashore for me to escape from.  And, again except for Carol, and my writing, which I can do anywhere, my real life is at sea.

Kevin (SFLF): Most of your voyaging and circumnavigations have been single-handed. What practical tips can you give to others who are considering long solo passages?  How do you handle the work (watch routines, repairs, navigation, etc.)?

Webb: What works for me works because I’m me and won’t necessarily be suitable or acceptable to others.

Navigation has changed over the decades.  On my first two circumnavigations I navigated by sextant, taking a sun sight in the morning when the sun was about 20° above the horizon—although there are refraction tables, I found them unreliable at lower angles—and another sight at local noon, and made a running fix.

Now I use GPS and use chartplotting software on my laptop(s) and iPad(s).  I’ll probably have two of each on GANNET, and an iPad mini with the iNavX app will probably be my primary.  Of iNavX, I will say that it does the job, but I am not completely satisfied with it.  The User’s Manual is inadequate and many actions unintuitive.

I have a sextant on GANNET, and do think that anyone going offshore would be well advised to know at least how to take a noon sight for latitude.

Of repairs, there is no set routine.  We’re talking about responding to unexpected breakage.  On THE HAWKE OF TUONELA I had a lot of spare nuts and bolts and good tools and could jury rig something.  On GANNET I can carry less, but then there is less to go wrong.

I don’t stand watches.  I sleep at night, waking often or not depending on where I am.  Near land I wake often.  The body and mind break down quickly from lack of sleep and water.  Food is a very distant third.  

Kevin (SFLF): I’ve got a wife and three daughters that love to sail and travel with me. For the most part, they share (tolerate?) my raw passion and desire to cruise under sail. I can’t imagine undertaking a long voyage without them, yet I’m fascinated by people who can make epic voyages single-handed. I guess what I'm wondering is how do you feel about the social aspects of solo sailing on long voyages? How do you deal with the solitude? Leaving loved ones behind? Do you feel the need to socialize and talk with other people when you reach an anchorage or make landfall?

Webb: I’m an only child and it took.  I’m used to being alone.  It is natural for me.  I enjoy entering what I have called the monastery of the sea.  But I am also much married.  I try to find a balance.  Obviously I haven’t always been successful.

Of children, I knew from certain deficiencies in my own childhood that parents owe their children time and love, and that children are  not a responsibility consistent with the way I want to live, so I had none.

I talk to people in anchorages, but am not desperate to do so the minute I get the anchor down. 

When I reach port, what I want most is a hot shower and a cold libation.

Kevin (SFLF): Do you ever get scared when you’re offshore? I imagine that Cape Horn and Southern Ocean sailing can be intimidating, particularly for a single-hander.

Webb: The animal inside all of us that always wants to survive becomes alarmed when conditions are threatening, particularly when they get out of control, so I’ve been frightened when waves have thrown my boats around, sometimes masthead in the water.  But I am not intimidated by the sea, not even the Southern Ocean.  I don’t claim to have courage.  Courage is doing something you are afraid to do.   Often people are afraid of the unknown.  I’ve spent years—I’m not sure how many, four or five, maybe more—at sea making passages and more than a year in the Southern Ocean.  The sea to me is not the unknown.

Kevin (SFLF): The boats you have owned and used for your circumnavigations represent unique choices. Many are not what I think a lot of mainstream cruising sailors and dreamers picture as bluewater cruising sailboats. For example, your Drascombe Lugger was a very small, open and unballasted boat; a daysailer by most accounts. Even your current sailboat, a Moore 24, is more of a light displacement racer than a long distance cruiser. What influences your choice in sailboats and what do you consider the most important features for an offshore cruiser?

Are oars considered "mainstream" on a cruising boat?

Webb: Of the mainstream, in any field, I think of Warren Buffet’s quote, “Be fearful when others are greedy, and be greedy when others are fearful.

My boat choices have often been to interest me and to explore limits.  

After my first circumnavigation, in which I became the first America to sail alone around Cape Horn and broke Sir Francis Chichester’s record for the fastest solo circumnavigation in a monohull by more than three weeks, I began seeking a qualitatively different challenge, thus the open boat voyage.

With GANNET, I wanted a new-to-me sailing experience.  While they’ve often been raced successfully from California to Hawaii, no one has ever gone farther in a Moore 24.  Being an ultra-light, the boats can surf.  I expect to reach speeds I never have under sail in my other boats, though CHIDIOCK TICHBORNE did peg her knotmeter at 10 knots at times in gale force winds.

I want a boat that sails well.  The most important quality of a sea going boat is that she be well built, regardless of size.  CHIDIOCK TICHBORNE and GANNET both were.  Everything else is secondary; and I learned long ago that it is often easier and always cheaper to adapt yourself to the boat than adapt the boat to you.

Kevin (SFLF): While I don’t think I’ve ever met a sailboat I didn’t like, my favorites are traditional salty double-enders with a full keel. I’m also smitten with pocket cruisers like the Pacific Seacraft Flicka. What’s your experienced opinion of my list of favorite pocket cruisers?

Webb: I prefer boats that sail better than heavy, full keel boats; but that is just a personal preference. 

When I looked at your list I was struck by one thing:  they are all expensive.  To check, I went online and found prices for all but the Tom Thumb, ranging from $30,000 to more than $100,000, with an average probably around $40,000.  This is more than I have ever paid for a boat.  Maybe $40,000 is nothing to most people, but it is to me, and I would think that if someone wants to “go small, go simple, go now,” and has $40,000, they would do better to buy a boat for less than $10,000 and keep the cash.  

I paid $9,000 for GANNET.  I know of a man preparing to sail away on a Cal 27.  When I was sailing CHIDIOCK TICHBORNE, a man was circumnavigating on a Catalina 27.  These aren’t my favorite boats, but they will get the job done.

[Editorial note: While Webb is correct in pointing out that a lot the boats on my list of favorite pocket cruisers can be pricey, I also wrote a post titled Blue Water on a Budget: 5 Budget Cruisers for Crossing Oceans that has vessels readily available for $10-15k.]

Kevin (SFLF): While I don’t know you personally, I get the sense that you’re definitely someone who enjoys the journey more than the destination.  Is that fair to assume?  What do you like most about being on passage and away from land? Anything you dislike?

Webb: What I like most has been answered on the introduction and credo pages of my site mentioned above.  

What I like least is provisioning for a long passage and, although I haven’t often had problems, dealing with officials when clearing in, when I’m usually tired from having limited sleep the night before.  I try to time landfalls for dawn.

Kevin (SFLF): For the sake of balance, let’s talk about some destinations. What are some of your favorite places that you’ve visited while circumnavigating? Any particularly memorable landfalls? Are there any places off the beaten path (away from the Caribbean, Pacific Milk Run, etc.) that you think more sailors should have on their itineraries?

Webb: First I reject the cliché, Milk Run.  There is no such thing.

Good destinations depend on personal preference.  I like New Zealand,  particularly the Bay of Islands, where I based THE HAWKE OF TUONELA for several years and am headed for next year in GANNET.  I like Australia, South Africa, the Azores—though the harbors were too crowded when I was last there in 2001.  Rio de Janeiro had a marina near the heart of the city and is so distinctively beautiful it looks like something from science fiction.  French Polynesia has two of my favorite anchorages in the world, one just inside the reef at Moorea, the other inside the reef at Bora-Bora.  Australia’s Lord Howe Island in the Tasman is as beautiful as any and seldom visited.  And my favorite coastal sail in the world is the 600 miles inside the Great Barrier Reef from Cairns, Australia, to Cape York.

Webb working the lines in New Zealand's Bay of Islands (2012)

Kevin (SFLF): Lots of cruisers use VHF/SSB radios and modems to receive digital (GRIB files) and verbal forecasts. I’ve heard that you typically use nothing more than a barometer and the sky for weather forecasting. Has this been reliable? Can you talk about how you use forecasts and account for weather when voyaging?

Webb: I think too many sailors worry about the weather when they can’t do anything about it. 

On a passage I naturally am paying attention to the sky and the sea and the barometer.  At sunset I look around.  What I’m seeking is change—in the clouds, the size and direction of the waves—just the feel of how the boat is moving.  I have had false positives, times when I’ve thought something might happen that night and it didn’t; but I don’t ever recall thinking, it’s going to be all right tonight and it wasn’t.

I pay attention to weather forecasts before I leave port.  I don’t want twenty plus knot headwinds at the start.  Beyond that I have confidence that I can adapt to whatever happens.

Kevin (SFLF): You’ve set several sailing records such as being the first American to solo around Cape Horn and probably have the most unsponsored, non-racing circumnavigations of anyone on the planet. Are any of these important to you and have records or notoriety ever factored into your plans?

Webb: We all take pride in different things.  One that I do is that I’ve set world records and never held a press conference.  I’ve made my voyages to please and interest myself.  I’m glad that others read what I write; but I would have sailed as I have if no one else ever knew.

Of what I’ve done that is most important to me, I still know that on December 12, 1975, I became the first American to round Cape Horn alone; I like the CHIDIOCK TICHBORNE voyage; I’m amused that I’ve lived long enough to become old and can still do my age in push-ups, and regularly do; and I’m curious as to what the GANNET voyage will bring.

Kevin (SFLF): What’s the motivation behind that upcoming 6th circumnavigation attempt?  Do you expect anything different out of that voyage than from your previous five, particularly considering that you’re now into your 70’s and have “been there, done that”?

Webb: My first and fourth circumnavigations were purely about the sailing.  The next will be, too.  I’m looking forward to seeing the Bay of Islands again, but will probably only stop two or three times all the way across the Pacific.

Three questions interest me about the voyage:  can 2050 pound, ultra-light GANNET endure?  can 72-year-old me endure?  And, will I take her to Cape Horn?  I’m suspending judgement on this last one until I’ve sailed the 6,000 miles to New Zealand.  

Gannet sits ready at the dock

Kevin (SFLF): You wrote on your website that your wife, Carol, has predicted that you’ll die by falling off a boat in the middle of the ocean when you’re 90. Would a death at sea be a fitting way for Webb Chiles to go? 

Webb: Absolutely.  But in fact I’ve already won the game by lasting far longer than anyone, including me, expected.

Kevin (SFLF): Do you ever think about your mortality when you’re far offshore?

Webb: No more than when I’m ashore, with the exception that I always am aware that one slip and I’m gone.  People worry about the statistically unlikely, when the mundane is a much more real danger.

Kevin (SFLF): If you were writing your own epitaph, what would you say? In other words, can you sum up your life on the sea in a sentence or two?

Webb: If I don’t die at sea, I strongly don’t want to be buried in a cemetery and have a tombstone.  I hope Carol will have me cremated and disposed of at sea, preferably off Cape Horn, but that might be asking too much.

Probably my two best known lines, found on the home page of my site, would do:

Live passionately, even if it kills you, because something is going to kill you anyway.

A sailor is an artist whose medium is the wind.

And in that vein, one could write on the hopefully illusory tombstone:

An artist of words, wind and women.


  1. Heck of a good read. I recall his piece from years ago when his boat sank under him off Florida (I think) and what he thought of while treading water.

    1. Thanks Rhys. Yup, Webb's sinking off Florida is a keystone moment in his career, I believe.

  2. Dave Mancini10 December

    Terrific interview of a great sailor and writer. Good job!

    1. Thanks Dave! I enjoyed putting the interview together.

  3. John Dean03 January

    Enjoyable interview, Typically Webb, says what he means and means what he says.

    1. Yup, Webb doesn't mince words and is clearly able to speak his mind, no matter the audience.

  4. Webb Chiles one of the best sailor all the time, safety travels!

  5. "This is more than I have ever paid for a boat. Maybe $40,000 is nothing to most people, but it is to me, and I would think that if someone wants to “go small, go simple, go now,” and has $40,000, they would do better to buy a boat for less than $10,000 and keep the cash."

    This is a quaint assertion but implies Webb has no comprehension of inflation. He bought his Ericson 37 new from the factory in 1973 for, what was it, $25,000? In 2023 dollars he paid $172,889 for that boat! This is a common thread amongst sailors from the 70's: they truly have zero comprehension of how little a dollar buys in the modern world, while wages have been stagnant since they shoved off and stopped working.


Post a Comment

Popular posts from this blog

Top 10 Favorite Affordable Bluewater Sailboats

Go Small and Go Now! 5 Pocket Cruisers to Take you Anywhere

Escape to the Sea: How to get from the Great Lakes to the Caribbean