Top Ten Most Inspirational Sailors

I originally planned to make a blog post about the 10 Best Sailors, but I quickly realized Im in no way qualified to assemble such a list.  However, I can confidently say which famous sailors have most influenced and inspired my own life.  My list focuses on famous sailors known to many.  Truth be told, there are many more ordinary everyday Joe/Jane type sailors who have inspired me every bit as much as those in my list below, but theyll be the topic of a future blog post.  And so, I present to you my personal list of the Worlds Top Ten Most Inspirational Sailors.   

10) Francis Chichester: The favored route around the world by cruisers today is by far the east-to-west "milk run" that roughly follows the trade winds near the equator.  Chichester instead sailed solo around the world from west-to-east in 1967, rounding all of the great capes (Cape of Good Hope, Cape Leeuwin, and Cape Horn) via the "clipper ship route".  Not only does this route pit sailors against some of the worst potential weather in the world, it is also counter to the trade winds.  As if that weren't enough, Chichester set the speed record around the world at just 226 days.

Watson's very pink boat.

9) Jessica Watson: Have you heard of Jessica Watson?  She's been in the news a lot the last couple of years.  She now holds the record for being the youngest person to ever sail solo unassisted and non-stop around the world.  She earned the record in May of 2010 when she returned to port in Sydney, Australia.  Here's the astonishing part: Jessica was just 16 years old!  I'm not a fan of all the publicity that these sorts of stunts purposefully attract, but I have to say that this is still a VERY impressive accomplishment.  Abby Sunderland is another name you may know if you're aware of Jessica Watson.  Abby also attempted to set the same record in 2010, but was dismasted in the Indian Ocean and had to be rescued at sea, thus ending her attempt.  Her brother Zac Sunderland also held the record for a brief period.  A third young female sailor, Laura Dekker from Netherlands, had plans to break the record at the age of only 14, but a Dutch court stepped in and delayed the record-breaking attempt.  She was eventually able to begin her attempt in 2010 and is currently in the Atlantic ocean close to completing her voyage after over 500 days at sea.  I have two daughters of my own and love to see them learning to sail and chasing dreams of their own.  However, I most definitely would not allow an attempt at these kinds of records.  Of course, if they wanted to leisurely sail around the world, I'd happily serve as crew.  I was initially hesitant to include Jessica in this list, but even my own parental trepidation can't deny her inspiration.  Stay tuned for a future blog post expressing my thoughts on these young record seeking sailors.

8) Peter Blake: As I've said in many other posts, I'm not a racing sailor and don't have any interest in winning races or setting records.  However, there are some sailors who have been so profoundly successful in racing sailboats that I can not help but be inspired.  Blake is just such a sailor.  He won the Whitbread Round the World Race and in so doing set the record for the fastest circumnavigation at just 74 days, 22 hours, 17 minutes and 22 seconds.  He also skippered dominating wins in the 1995 and 2000 America's Cup yacht races for his home country of New Zealand.  He was tragically killed in 2001 by pirates while on an environmental expedition in Brazil on the Amazon River.  Blake is easily one of the most recognized names in modern sailing and is at the top of many people's "Top Ten Sailors" list.

7) Webb Chiles: "A sailor is an artist whose medium is the wind."  I love that quote by Webb Chiles and often think of it as I'm trimming my sails and trying to get the boat into that perfect rhythm.  As a writer, Chiles has authored seven books and published hundreds of articles.  As a sailor, he's completed five circumnavigations and holds several world records and long ago became the first American to sail alone around Cape Horn.  In his words, he "wanted to live an epic life".  He has plenty of skeletons in his closet (six marriages, etc.), but he's always good for a salty and thought provoking quote.  For instance, try to digest this gem: "I believe that the artists defining responsibility is to go to the edge of human experience and send back reports."  If you long for more, check out Webb's website (or is it webbsite?) at In The Present Sea.

Kon Tiki in 1947
6) Thor Heyerdahl: The Kon-Tiki expedition is remarkable in so many ways.  Imagine building a sailing raft by hand, using only the natural materials that would have been available to primitive people from thousands of years ago.  Heyerdahl did just that when he built the Kon-Tiki.  Even more remarkable is the journey Heyerdahl completed aboard his homemade sailing raft.  He set out from South America in 1947 bound for the islands of French Polynesia.  Heyerdahl theorized that the aboriginal settlers of the once uninhabited South Pacific islands originally came from South America.  After 101 days at sea and over 4,300 miles of blue Pacific Ocean, he landed on a reef at Raroia in the Tuamotu Islands.  Though most modern anthropologists now have different theories about how the South Pacific was first discovered and populated by humans, I have major respect for a man who took such massively courageous steps to prove the feasibility of his theory and beliefs.  If you want to learn more about Heyerdahl and the expedition, I highly recommend the book Kon-Tiki written by Heyerdahl.

Joshua Slocum

5) Joshua Slocum: Sailing single-handed around the world these days is still a major feat, but being the first to do so is truly deserving of this list.  Some said his wooden boat Spray wasnt up to the task, but he proved the naysayers wrong when he finally returned to Newport, Rhode Island in June of 1898 after completing the 46,000 mile circumnavigation.  His book, Sailing Alone Around the World, is a travel and sailing classic.  Slocum disappeared in 1909 when he set sail for the Caribbean.

4) Ferdinand Magellan: I'm both fascinated and frightened to imagine circling the globe aboard a sailing vessel 500 years ago.  500 years ago!  While Magellan himself died on the voyage, his expedition and some of his crew are credited with the first circumnavigation of the planet Earth.  Many of todays geographical landmarks either bare Magellans name or were named by Magellan.  Of particular note are the Pacific Ocean (Mar Pacifico in Portuguese, meaning Peaceful Sea) and the Strait of Magellan.

3) Robin Lee Graham: The 1960s were in many ways the dawn of the cruising sailboat era.  Graham was a pioneering cruiser and the precursor to the recent slough of youngsters attempting to become the youngest person to sail around the world (see Jessica Watson above).  Graham began his epic solo voyage around the world on a 24 foot sailboat when he was just 16 years old.  He completed it at the age of 21 in 1970.  Graham's book about his experience (Dove) is one of my all-time favorites.

2) Bernard Moitessier:  Cruising aboard a sailboat would quite simply not have the deep meaning that it does today for so many of us without Moitessiers inspirational words and foundational world cruises.  Moistessier was one of the first to discuss a non-stop, around the world solo race and eventually competed in the initial event when it finally came to be known as the Sunday Times Golden Globe (known today as the Vendee Globe) in the late 1960s.  He ended up quiting the race but continued on around the world almost one and two-thirds times before finally stopping to recharge in Tahiti.  He was never about racing, speed or winning but rather finding himself and challenging his sea-hippy spirit.  That statement could well describe myself.  The following is a Moitessier quote from one of his books, The Long Way, that I recently received as a gift (Thanks Dad!): My real log is written in the sea and sky; the sails talking with the rain and the stars amid the sounds of the sea, the silences full of secret things between my boat and me, like the times I spent as a child listening to the forest talk.

1) James Cook: No list of great sailors would be complete without mention of Captain James Cook.  His three epic voyages of discovery in the late 1700s helped lay the groundwork for nautical charts still in use today.  Cook is credited with being the first European to discover the Line Islands archipelago (including Hawaii), the first European to set foot on Australias eastern shoreline, the first person to very accurately map the entire coastline of New Zealand, and the first to chart most of North Americas northwestern coastline.  Cook also put to rest Aristotles notion of Terra Australis, the great southern continent thought to include all of todays Antarctica, Australia and New Zealand. Countless locations on todays maps owe their modern names to Cook and his voyages (Botany Bay, Cooktown, Endeavour River, New Caledonia, etc.)  Of particular note are the Hawaiian Islands, which Cook originally named the Sandwich Islands after John Montagu, the 4th Earl of Sandwich.  [Free tidbit: Lord Sandwich himself is the reason we call two slices of bread separated by meat a sandwhich.  Apparently, Lord Sandwich had a habit of requesting his meat be placed between slices of bread when playing cards and ever since the combination has been called a sandwich.] 

John Webber's 1776 oil painting
of Captain Cook
While much of Cooks story comes acrossed as roses, there were plenty of thorns.  Cook and his crews typically had good relations with the native South Pacific islanders and in particular the Hawaiians, but this ended after a dispute over small boats being stolen from Cook.  The confrontations and quarrels that followed led to James Cook being killed on the beach at Kealakekua Bay on the big island of Hawaii.  In addition to the notable achievements listed above, Cooks voyages are also often credited with introducing venereal disease, alcohol and firearms to many cultures in the South Pacific that had previously been untouched by the woes of Western civilization. 

The South Pacific looms large in most modern day cruisers dreams, including my own.  While much has changed there since the 1700s, the mystique of an isolated tropical paradise still remains.  The islands of the South Pacific remain a long passage from any mainland and the blue horizons on such a passage are the same as Cook would have seen.  I cant help but picture myself feeling like Captain Cook if Im ever fortunate enough to make the milk run to Polynesia.  Researching and reading about Cooks voyages has fascinated me for years.  If youre interested in learning more about Cook, I highly recommend Tony Horowitzs book Blue Latitudes: Boldly Going Where Captain Cook Has Gone Before.  Cooks embodiment of the words explorer, captain, and sailor are what easily puts him at the top of my most inspirational sailors list.      


  1. Hi Ted . . . When a list has to be reduced to only 10 I understand it is diffuclt to chose, but I believe you left out one of my sailing heros, Robin Knox Johnston. Sir William Robert Patrick "Robin" Knox-Johnston, CBE, RD and bar (born 17 March 1939) is an English sailor. He was the first man to perform a single-handed non-stop circumnavigation of the globe and was the second winner of the Jules Verne Trophy (together with Sir Peter Blake). For this he was awarded with Blake the ISAF Yachtsman of the Year award. In 2006 he became at 67 the oldest yachtsman to complete a round the world solo voyage in the VELUX 5 Oceans Race.

    1. David - RKJ is certainly worthy of my list, but as you said, I had to cut it off somewhere. (FYI - While Ted Brewer has written several guest posts on my blog, unless otherwise noted, all the content here has been authored by me, Kevin Walters.)

  2. OK Kevin, I misunderstood whose blog it was. Ted Brewer sent me the link. Now I understand . . . anyway, it is a great blog. Thanks for sharing. I was captain of the yacht Mystic for two different owners, including the original owner Marvyn Carton. You can see my biography at

  3. Anonymous17 March

    I, personally, was touched by Robert Manry.

    1. Ah yes, Manry and his boat Tinkerbelle. He's definitely worthy of mention on a list of inspirational sailors. Thanks for sharing!

  4. Anonymous01 May

    I'm sorry, Mr. Walters, but I can't help noticing that every person you have on this list is white. You would be wise to either revise or give reasons as to why this is.

    1. As I menionted in the opening paragraph, these are merely the sailors who have influenced and inspired my own life. I didn't mean to put this out there as a definitive list for all people, but rather my opinion on the matter. Feel free to share your own most influential and inspirational sailors here in the comments. In any case, thanks for reading and commenting!

    2. john emmerton26 August

      A sailor is a sailor........who cares about the skin colour....!

  5. Anonymous21 January

    Don't forget about the legendary Vito Dumas

    1. Thanks for the addition! I hadn't heard of Vito before, but I just read the Wiki page and wow...single handed circumnavigation of the Southern Ocean a 31-foot ketch in 1942...very cool!

  6. Anonymous05 June

    1) Piri Reis


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