The 10 Best Sailing Stories Ever Written

S/V Tres Hombres

If you’re anything like me, you know the beauty of nestling yourself into a sailing story after, or during, a long day on the water (while listening to some sailing music, perhaps?). Even if you didn’t spend any time on the water, these books tell of exciting adventures at sea, ripe with beautiful scenery and thrilling action. My fellow sailors out there know the connection to the sea that comes from reading a good sailing book. Whether they are fictional, non-fictional, or something in between, they all have one thing in common: a connection to the sea, which can unforgiving, powerful, and beautiful all at once.

For this article, I’m going to offer a peek inside my personal collection. After many years spent working and bumming around sailboats, I’ve come across my fair share of sea adventure stories, and even racked up a few of my own.

Find below a list of what I consider to be 10 the best sailing stories ever written.

1. Sailing Alone Around the World by Joshua Slocum

Famous for being the first person to sail solo around the world, Joshua Slocum came home and wrote a memoir about his experiences, the aptly-named Sailing Alone Around the World. Slocum set sail from Boston, Massachusetts in April 1895 on a 37 foot wooden boat, his gaff rigged sloop named the Spray. Sailing Alone Around The World recounts Slocum’s experiences over the next three years until his return to Newport, Rhode Island in June of 1898.

Sailing Alone Around the World is a fascinating sailing memoir about something that most sailors have thought about one day doing, except most of us wouldn’t attempt it alone. Slocum encounters pirates, storms, and catches fish for breakfast, taking us with him to each place he visits and showing us the culture and the people that exist there.

This sailing story has become a classic piece of travel literature, and is one of the most amazing books about sailing that exists. Slocum has been an inspiration for many sailing voyages since his time. If you’re looking for a place to start in terms of sailing adventure books, you can’t go wrong with Sailing Alone Around the World.

2. Master and Commander by Patrick O’Brien

The first in the acclaimed Aubrey & Maturin series by Patrick O’Brien, Master and Commander is a sailing novel that begins the story of the young Captain Jack Aubrey as he takes command of a ship in the Royal Navy during the Napoleanic Wars. At the core of Master and Commander, and really the entire Aubrey & Maturin series, is Jack’s friendship with the Irish naturalist and physician Stephen Maturin.

This book is what inspired the fantastic 2003 movie of the same name. It’s an epic sailing novel filled with adventure, and at times can seem dense with nautical terminology, but that’s what makes it special in a literary sense. Master and Commander a tale of leadership, friendship, war, adventures at sea, and sailing that is a must-read for sailors and landlubbers alike.

Once you read Master and Commander, you’ll want to keep going, and luckily for you, you certainly can. There are 20 total books in Patrick O’Brien’s Aubrey & Maturin series, and I recommend every single one of them. The friendship between Jack Aubrey and Stephen Maturin continues to evolve over the course of the entire series, through wartime and many miles on the open ocean, and O’Brien takes advantage of it to weave some of the best sailing novels of all time.

3. Endurance: Shackleton’s Incredible Voyage by Alfred Lansing

Endurance: Shackleton’s Incredible Voyage is a nonfiction story recounting of the voyage to the Antarctic taken aboard the sailing vessel Endurance in 1914. Led by Edward Shackleton, the three-masted barquentine Endurance departs on a mission set on crossing the Antarctic continent on foot, a feat which at the time had not yet been accomplished. The ship gets stuck in pack ice in the South Weddell Sea and after spending a winter frozen in place, with the crew of 28 still on board. When the Endurance eventually sinks, Shackleton leads all 28 men on a nearly two year journey on foot, surviving against all odds.

Perhaps the most amazing part of this sailing story comes in the final portion of the book, when Shackleton and five other men cross the Drake Passage (the world’s most treacherous body of water) on a 20 foot wooden sailboat in sub-zero temperatures and 40 to 60 foot seas. Somehow the men survive and go back to rescue the rest of the crew which was left waiting on a frozen island, surviving off penguins and seals with no other option, fantasizing about an extremely unlikely rescue.

The story of Endurance is as much a book about sailing as it is a book about leadership. It’s incredible to think that Shackleton was able to keep every single man alive in these conditions. Lansing used firsthand accounts to stitch his story together, even obtaining original copies of the crewmen’s journals to ensure his information was accurate, and manages to do justice to the thrilling story of Shackleton and the Endurance.

4. A Voyage for Madmen by Peter Nichols

In 1968, the British Sunday Times sponsored the Golden Globe Race, for which they were offering the first person to complete a non-stop solo circumnavigation on a sailboat a trophy and a cash prize. Peter Nichols’ A Voyage for Madmen tells the story of the nine sailors who competed in the race and their experiences and adventures at sea. Out of all nine sailors who took part in the race, only one of them, Robin Knox-Johnston, actually finished.

A Voyage for Madmen is a tense, suspenseful and compelling sailing story that will keep you on the edge of your seat for the duration. Don’t be surprised if you get sucked in and read the entire book in a short time span, because this is definitely one of those. Not only will you read about what these men went through from a sailing standpoint, you’ll also get some insight into their psyche and what can happen to the mind when you’re out on the water alone for extended periods of time.

In fact, Nichols’ ability to portray the characters of the nine men who partook in the Sunday Times Golden Globe Race is perhaps the most compelling aspect of A Voyage for Madmen. Each man has a different background, different motivations for entering the race, and a different set of outcomes, some, even, that are fatal.

5. The Long Way by Bernard Moitessier

Yet another book about the famous Sunday Times Golden Globe Race, this one is an autobiographical account of one contestant’s experience. Bernard Moitessier took part in the race but unlike the other contestants, he was already rich and thus not particularly interested in the prize, but rather just wanted the adventurous experience and spiritual journey of sailing alone around the world. His book The Long Way tells his story.

Moitessier started the race just like everybody else, but instead of finishing the race in England, he decided to keep going. He was on board a 39 foot steel ketch named Joshua, and ends up sailing one and a half times around the world before going to Tahiti and having a son with a women he met there. Moitessier would have kept going, and was considering rounding Cape Horn a second time for the hell of it, but decides that his boat has taken enough of a beating and heads in.

The Long Way is one of those sailing stories that reminds you that sailing is all about the connection with nature and yourself that can only come from being out in the mercy of the elements. In his book, Moitessier focuses on the personal experience he had while being out at sea alone for seven months straight, sailing for the joy of it and enjoying the things he finds along the way.

6. The Sea Wolf by Jack London

Jack London’s 1904 novel The Sea Wolf tells the story of literary critic Humphrey van Weyden who departs on a ferry that sinks, leaving him adrift until he’s picked up by Captain Wolf Larsen of the seal hunting schooner the Ghost. The Sea Wolf is a sailing novel, but it’s more of a psychological adventure that explores the relationship between a brutal leader and his shorthanded crew.

Written by one of the all-time great American authors, The Sea Wolf is an exciting read that serves as a study of human nature told through the lens of the high seas. Jack London was a man of the sea himself before becoming a novelist, and that often shines through in his work. This is certainly true with The Sea Wolf, a story of sailing adventure and hardships told through stunning prose.

7. Once is Enough by Miles Smeeton

Though somewhat lesser known, Miles Smeeton’s autobiographical sailing story Once Is Enough is one of the best books about ocean sailing ever written. It’s about the experience of three people on board a small ketch, the Tsu Hang in the Southern Ocean after departing from Australia with intentions to round Cape Horn. Smeeton tells his story like a true Britishman, facing situations that are likely to kill less experienced sailors with a straight face and a lack of fear.

Once Is Enough is told in a light manner in a writing style that overflows with a love for life and adventure. Smeeton and his companions are determined to survive, spending time jerry-rigging their dismasted boat and making it back safely, but not before capsizing for a second time…

8. The Incredible Voyage by Tristan Jones

Oh, Tristan Jones, where do I begin. For those who aren’t familiar, Tristan Jones was a man who spent a lot of time swashbuckling around the Mediterranean Sea, and decided at some point to reinvent his past and become a writer. He’s was for heavy drinking, starting fights, and writing awesome sailing memoirs in which he claims to have done things that he definitely didn’t actually do.

With that out of the way, The Incredible Voyage tells the Tristan Jones story of a six year voyage that covers two times the circumference of the world. The Incredible Voyage is a “nonfiction” sailing adventure book that includes a lot of brazen and obvious lies, and sometimes even contradictions within a few paragraphs of one another, but that’s part of the fun. Tristan Jones’ sea stories are as much about enjoying the character of the author as they are reading about the actual adventures.

9. Adrift: Seventy-Six Days Lost at Sea by Steven Callahan

Steven Callahan’s Adrift: Seventy-Six Days Lost at Sea is a sailing story about a man who capsizes and loses his boat just six days after setting out alone from the Canary Islands en route to Antigua. He spends the next 76 days alone on a life raft, drifting in the open ocean and doing whatever it takes just to stay alive.

Adrift: Seventy-Six Days Lost at Sea dives into Steven’s psychological state during the situation, and is a testament to the resilience of human nature when it is truly put up to the test. Steven survives thanks to his nautical knowledge and the determination to make it back alive. This is yet another incredible nonfiction account of sailing adventure and something that should be on the shelf of any sailor or survival story enthusiast.

10. Carry On, Mr. Bowditch by Jean Lee Latham

Another true story of sailing adventure, Carry On, Mr. Bowditch tells of Nathaniel Bowditch, a man who in his early life had little hope of becoming a sailor. He was too small, too weak, and nobody thought he had the mental fortitude to do it. Turns out, the kid was a mathematical genius, and ended up becoming of the best navigators that has ever lived, writing a famous book called The American Practical Navigator.

Bowditch endures many hardships during his lifetime, but thanks to his intelligence and determination, he is able to find success through even the worst of times. Carry On, Mr. Bowditch is an inspiring read that can be enjoyed by anyone with an interest in sailing, navigation, or the human spirit.

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