There is something magical about a great sailing book. Whether you’re an experienced sailor, aspiring cruiser, or just someone who dreams of escaping to the open ocean, the right book can transport you to life on the ocean, teach you invaluable lessons, and even make you feel like you’re side by side with the author.
Over the years, countless sailors have documented their adventures—some triumphant, others tragic, but all inspiring. These sailing legends have shared practical knowledge and countless stories gained from a lifetime at sea, offering wisdom that can make all the difference for those looking to start their own adventures.
Throughout many years of reading and studying sailing, I put together a list of some of my favorite sailing books, divided into categories so you can easily find what interests you most. Whether you’re craving thrilling survival stories, solo circumnavigation accounts, or practical guides for your own journey, there’s a book on this list for you.
Keep in mind these are only SOME of MY favorite sailing books. I know there are many other amazing books from other amazing sailors.
Solo Sailing & Extreme Voyages – For those fascinated by the ultimate test of single-handed sailing
The Long Way – Bernard Moitessier
Moitessier was a competitor in the 1968 Golden Globe Race, a solo, non-stop circumnavigation. For months, Moitessier battled storms, doldrums, rig failures, knockdowns, and fatigue. Once he was approaching the finish, he pulled out of the race and kept sailing for another three months, ending his over 37,000-mile voyage in Tahiti. This is a classic sailing story from a pioneer that belongs in every sailor’s library.
Sailing Alone Around the World – Joshua Slocum
Another sailing pioneer, Joshua Slocum was the first person to sail around the world single-handed aboard his sloop Spray in the late 1800s, taking him over three years! His gripping memoir details encounters with pirates off Gibraltar, storms around Cape Horn, rogue waves off Patagonia, coral reefs, and more! If you’re looking for a jaw-dropping book about an epic adventure, this book is for you.
Alone Through the Roaring Forties – Vito Dumas
Vito Dumas took on one of the most dangerous sailing routes, battling the Southern Ocean in his 31’ wooden ketch. His determination and resilience through severe infections nearly forcing him to amputate his arm, scurvy, severe storms, and more challenges shine in this tale of grit and survival.
Sailing into Oblivion – Jerome Rand
A modern-day story of solo sailing, Sailing into Oblivion follows Jerome Rand’s incredible nonstop circumnavigation aboard his Westsail 32 Mighty Sparrow. His experience is raw, emotional, and filled with valuable lessons about self-reliance as he battles storms, lack of food and water, and other challenges. His book features many entries from his logbook that give a unique insight into the mind of a solo sailor after nearly a year alone at sea, helping paint an incredible story that cements him as modern-day sailing legend.
Ocean Voyages and Survival at Sea
Cape Horn to Starboard – John Kretschmer
John Kretschmer needs no introduction. A great sailor and author, Kretschmer seems to have endless stories and knowledge about sailing. Cape Horn to Starboard tells the story of a young John Kretschmer who retraced the Clipper Ships’ route and doubled Cape Horn the wrong direction with his friend Ty aboard his Contessa 32, Gigi. This story combines adventure and struggle that will make you feel a deep appreciation for the raw power of the ocean.
Sailing to the Edge of Time – John Kretschmer
Another John Kretschmer classic, this book shares John’s lessons learned from decades sailing around the world. Offering a more philosophical take on sailing, this book is great for offering insight for both seasoned sailors, dreamers, and those who want to take a deeper dive into the philosophical side of sailing.
Imperfect Passage – Michael Cosgrove
A reluctant adventurer, Michael Cosgrove set sail at sixty to escape a midlife crisis—only to find himself facing life-threatening situations, and the reality of sailing. His honest and even humorous story does a great job of representing the highs and lows of offshore sailing. This book is great for sailors beginning their adventure, as it represents sailing from a beginner’s point of view as he’s learning.
In The Heart of the Sea – Nathaniel Philbrick
This is the true story of the whaleship Essex, which was attacked by a whale and left its crew stranded in the middle of the Pacific Ocean. This is perhaps one of my favorite books I have ever read and always one that I go back to whenever I can. This historical account of survival, starvation, and desperation inspired Moby-Dick and will leave you in awe.
At the Mercy of the Sea – John Kretschmer
A At the Mercy of the Sea is a heartbreaking yet gripping true story of three sailors caught in the path of Hurricane Lenny in 1999, later named “Wrong Way Lenny.” Kretschmer once again writes a masterful narrative about the unpredictable power of the sea.
Storms, Heavy Weather & Seamanship
Handling Storms at Sea – Hal Roth
Another great sailor and writer, Hal Roth wrote many books throughout his lifetime. This book is a practical and detailed guide to surviving extreme weather events at sea. Roth explores storm tactics, equipment, and real-life accounts from sailors who faced nature’s worst. Handling Storms at Sea belongs in every sailor’s library as it’s an invaluable asset for staying safe while offshore.
Sailing a Serious Ocean – John Kretschmer
Sailing a Serious Ocean is equal parts practical advice and thrilling storytelling. This book covers what it takes to sail offshore. Kretschmer’s personal experiences bring to life the challenges and rewards of offshore sailing while using his real-world experience to weigh the pros and cons of different equipment, hull shapes, rig types, etc.
Cruising & The Liveaboard Lifestyle
Flirting with Mermaids – John Kretschmer
Flirting with Mermaids is a humorous and heartfelt collection of stories from Kretschmer’s years as a yacht delivery captain, sailing a number of different boats of all shapes, sizes, and conditions to exotic locations while encountering unforgettable characters along the way. This book will have you laughing and wishing you were there on the boats with him.
Chasing the Nomadic Dream – Paul Trammell
Paul Trammell writes about leaving Massachusetts on his sailboat Windflower and making his way south to get out of the cold weather. Trammell is a very good writer and leaves out few details, giving you a good grasp of the highs, lows, and challenges a solo sailor goes through. He shares lessons learned, GPS locations of anchorages, and also a few poems and pictures to enhance your reading experience.
Cruising for Cowards – Liza Copeland
Cruising for Cowards is a must-read for any new sailor. It is a lighthearted yet highly informative book filled with tons of tips and advice for making cruising easier and more enjoyable.
Practical Guides & Sailing Instruction
How to Sail Around the World – Hal Roth
Another great Hal Roth book, How to Sail Around the World, is a step-by-step guide to preparing for a world voyage. Roth covers everything from choosing the right boat, provisioning properly, navigation, heavy weather tactics, and more.
Wiley Nautical Sail and Rig Tuning – Ivar Dedekam
I can accredit a lot of my sailing skills to this book. A small, colorful book with many pictures makes it easy for sailors to understand and optimize their rigging and sail trim.
Yacht Design According to Perry – Robert H. Perry
Bob Perry needs no introduction. His book offers a rare glimpse into the mind of a designer who understands both boats and the people who sail them.
Whether you’re dreaming of a solo circumnavigation, preparing for your own offshore adventure, or just love a good story, these books capture the magic, challenges, and wisdom of life on the water. From harrowing survival tales to practical seamanship guides, each book offers something valuable—whether it’s inspiration, knowledge, or just the thrill of the open ocean during a cold winter day.
If you’re looking to start your sailing dream, reach out today so I can help you get started today!
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TODD TISOSKEY
Yacht Broker – Brewer Yacht Sales |
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