The best books on sailboats

3 authors have picked their favorite books about sailboats and why they recommend each book.

Soon, you will be able to filter by genre, age group, and more. Sign up here to follow our story as we build a better way to explore books.

Shepherd is reader supported. When you buy through links on our website, we may earn an affiliate commission (learn more).

Sea Wife

By Amity Gaige,

Book cover of Sea Wife

Gaige’s writing is terrific, insightful, fresh, and fast-paced. As I read about the fictional couple and their conflicts at sea, I was struck by the similarities to our real-life sailing experience. In a fabulous first scene, the wife hides in a closet, unable to deal with reality. She reluctantly goes on a voyage with her husband and their lives change, much as ours did. I never hid in a closet, but before the voyage, I was someone who if I didn’t like reality, ignored it. At sea, that’s not possible. 


Who am I?

I have lived on or around sailboats for over thirty years. I had never sailed before meeting my husband. Many people dream of sailing off but few actually go. In 1996, we sailed away to the Caribbean with our seven-year-old daughter. Although I didn’t want to go, by the end of the voyage I found an inner strength that has stayed with me. The books I chose are all about making huge changes, taking leaps of faith. I hope you enjoy them as much as I have!


I wrote...

Holding Fast: A Memoir of Sailing, Love, and Loss

By Susan Cole,

Book cover of Holding Fast: A Memoir of Sailing, Love, and Loss

What is my book about?

Holding Fast: A Memoir of Sailing, Love, and Loss is Susan Cole’s story of leaving everything behind to follow her husband's lifelong dream of sailing away. Blond, blue-eyed, irreverent John bursts into Susan’s life in her twenties with dreams of sailing off. Susan dreams of settling down. A three-year voyage with their young daughter to the Caribbean profoundly changes their lives.

Susan’s journey took her from the glitzy world of Madison Avenue advertising to riding out Hurricane Mitch, the largest hurricane on record at the time, on a sailboat in Guatemala. She hadn’t wanted to go in the first place but ended up on a life-changing odyssey. A gripping adventure story and an inspirational memoir of finding our power in the unlikeliest of places.

The Wreck of the Zephyr

By Chris Van Allsburg,

Book cover of The Wreck of the Zephyr

High atop a cliff overlooking the sea sits the battered remains of a sailboat. But how did it get there? An old man insists that the waves had tossed it all the way up during a storm a very long time ago, although this clearly seems to be impossible. Or is it? In this magical tale of adventure, a young boy had aimed to prove that he was the most brilliant sailor his villagers had ever seen, so he set out to prove it. What happened when he was blown to a brand-new land, and did he survive? I have always enjoyed Chris’s artwork and you may have overlooked this particular book, so pick it up and check it out.

Who am I?

I am a spy aiming to uncover hidden documents, private journals, and secret messages penned in the distant past. I am a detective racing to reveal the world’s most dastardly deeds and daring escapades. I am an adventurer zooming around the planet along with history’s bravest heroes and most despicable villains. I am an artist whose illustrations transform ancient stone-cold statues by turning them into living, breathing human beings that laugh and cry, win and lose, love and hate, and spring vividly to life. And I am a storyteller striving to lure readers of all ages, whether they are children or adults.


My book is...

Witches: The Absolutely True Tale of Disaster in Salem

One freezing day in 1692, a preacher’s two young daughters began to choke and twist their bodies into strange abnormal shapes and speak in words that made no sense. But why? An elderly physician examined the girls and proclaimed that they were witches!! For centuries these horrid creatures had invaded the nightmares of suspicious souls around the world, and now the Devil himself had brought them all to Salem. A torrent of evil soon invaded the town. The King of Hell was captured, and many witches were jailed or hanged or worse. How did this happen? Read all about it if you dare.

Lila

By Robert M. Pirsig,

Book cover of Lila: An Inquiry Into Morals

I recommend the sequel to Pirsig’s more famous bestseller because I’ve never owned a motorcycle (and I find bicycle maintenance hard enough), but now I own a sailboat—where his second story is set—so when he describes hearing people walking on the cabin roof, or checking the knots on the mooring ropes, I know exactly what he means because I’ve experienced this. Some of his fans felt this sequel was a betrayal of the magical mysticism of undefined Quality he described in the first book. For me, although problematic, it was a necessary clarification and one I not only used for my academic work on a range of controversies from abortion to transgender but also in my life-coaching practice: to inspire holistic transformation on all levels of wellbeing. 


Who am I?

Scotland has a proud tradition of philosophical enquiry and I studied closely the work of most of these authors and benefited from almost all of them for my own Ph.D. work. Pirsig uses the old Scots word “gumption” for know-how and initiative and, in his honour, I use his related term “gumptionology” as my handle on social media. I also write my own mystery books series set in Scotland (the Bruno Benedetti mysteries) and they are often inspired by musing on philosophical and metaphysical matters but even my books on ethics contain some philosophical fiction. Our shared stories are fundamental to our humanity—and to our philosophy!


I wrote...

Alchemy at the Chalkface: Pirsig, Pedagogy and the Metaphysics of Quality

By Alan McManus,

Book cover of Alchemy at the Chalkface: Pirsig, Pedagogy and the Metaphysics of Quality

What is my book about?

“What the hell is Quality?” asked the author of my first book pick, halfway through his bestseller, prompted by a middle-aged colleague at Bozeman College (Montana) watering her office plants and asking him about his English teaching. He described that question as a seed crystal which grew into his two famous works of philosophical fiction then, mostly through misunderstanding, created a maze of educational and industrial regulations—provoking endless academic discussion over their justification and coherence.

50 years later, halfway through my doctorate in Scotland, suffering from painful RSI in my hands and wrists from typing obsessively in a damp ground-floor flat, trying to cram in every philosophical insight from Plato to Robert M. Pirsig, I decided, like these philosophers, to answer by telling a story.

The Strange Voyage of Donald Crowhurst

By Nicholas Tomalin, Ron Hall,

Book cover of The Strange Voyage of Donald Crowhurst

When a man sets sail on an extended ocean voyage, there is usually purpose, determination, and a goal to reach. Donald Crowhurst likely held these objectives when he embarked upon his round-the-world sailing adventure…but somewhere along the way, he lost sight of those goals, and seemingly with the basic truth of reality. Crowhurst’s story is a  sometimes dark and disturbing account of what the voyage was all about, and what may have actually taken place on this strange and bizarre odyssey. As a man who has felt the pangs, insecurities, and unknowns when on the ocean, miles from land, scared, and facing the challenges that both nature and humanity tossed our way, I can somewhat understand how a man at sea can become so lost, so confused, and so vulnerable.

The Strange Voyage of Donald Crowhurst helped me to understand some of the odd feelings and thoughts that I have…


Who am I?

I'm a man of the sea. From my early days as a boy growing up on the coast of southern California, I became a fisherman at age 5, when my dad took me fishing at the pier in Redondo Beach. In my teens, I bought my first boat that I used in and around King Harbor for fishing. After owning other small boats, I moved to Catalina Island where I worked for 32 years as Harbormaster, earning my 100-ton Masters License and broadening my ocean experiences. Eventually I wanted to share my stories and experiences through writing. My first book, Between Two Harbors, Reflections of a Catalina Island Harbormaster, tells my Catalina story.


I wrote...

Five Weeks to Jamaica

By Doug Oudin,

Book cover of Five Weeks to Jamaica

What is my book about?

Five Weeks to Jamaica is an action-packed adventure that follows four young friends on an exciting ocean voyage down the coast of Mexico, Central America, through the Panama Canal to Jamaica, and beyond. Their journey is filled with excitement, danger, romance, and the type of sexual interactions that one might expect on a 147' motor yacht carrying thirty passengers on an extended ocean cruise. From exotic ports to unexpected personal encounters and revelations, this seafaring odyssey will keep you raptly entertained.

The Voyage of the Cormorant

By Christian Beamish, Ken Perkins (illustrator),

Book cover of The Voyage of the Cormorant: A Memoir of the Changeable Sea

Building your own sailboat from scratch, then sailing it from California down to Baja, camping, and surfing along the way: how can that not be a cool story? Christian Beamish manages the perfect blend of introspection and backstory with descriptions of sea, sky, land, and the people he meets along the way.


Who am I?

As an avid trail-runner and mountain-biker who’s done a ton of outdoorsy things, from sailboat racing on the Chesapeake Bay to rockclimbing to backpacking in the Pacific Northwest, I’m convinced that nothing gets you closer to someone’s experience than a well-told first-person account. The best personal narratives make you feel the cold, glow with the exhilaration, and burn with ambition to go, to do, to see for yourself — and can even make you look at the world, and yourself, in a new way. These books, different as they are, have all done those things for me.


I wrote...

A Window to Heaven: The Daring First Ascent of Denali: America's Wildest Peak

By Patrick Dean,

Book cover of A Window to Heaven: The Daring First Ascent of Denali: America's Wildest Peak

What is my book about?

In A Window to Heaven, Patrick Dean brings to life this heart-pounding and spellbinding feat of this first ascent and paints a rich portrait of the frontier at the turn of the twentieth century. The story of Stuck and his team will lead us through the Texas frontier and Tennessee mountains to an encounter with Jack London at the peak of the Yukon Goldrush. We experience Stuck's awe at the rich Inuit and Athabascan indigenous traditions—and his efforts to help preserve these ways of life.

Filled with daring exploration and rich history, A Window to Heaven is a brilliant and spellbinding narrative of success against the odds.

Dove

By Robin L. Graham,

Book cover of Dove

Dove chronicles the story of a 16-year-old who sets off around the world on a tiny sailboat. For 5 years, while also covered by National Geographic, Robin tells his story of fighting storms, discovering new lands, and finding love. It’s an ultimate coming-of-age manifesto, full of inspiration and guts.


Who am I?

I am Zoltan Istvan, often considered one of the world’s most visible transhumanists. I began my career at National Geographic, but then turned towards leading the radical science movement forward that is now called transhumanism. We want to upgrade the human being with radical technology and overcome biological death. But all great movements need journies, and leaders of them need personal journies to be inspired by. These 5 books were the ones that inspired me the most!


I wrote...

The Transhumanist Wager

By Zoltan Istvan,

Book cover of The Transhumanist Wager

What is my book about?

Scorned by over 500 publishers and literary agents around the world, his philosophical thriller has been called "revolutionary" and "socially dangerous" by readers, scholars, and religious authorities. The novel debuts a challenging original philosophy, which rebuffs modern civilization by inviting the end of the human species—and declaring the onset of something greater. The novel tells the story of transhumanist Jethro Knights and his unwavering quest for immortality via science and technology. Fighting against him are fanatical religious groups, economically depressed governments, and mystic Zoe Bach: a dazzling trauma surgeon and the love of his life, whose belief in spirituality and the afterlife are absolute. Exiled from America and reeling from personal tragedy, Knights forges a new nation of willing scientists on the world's largest seasteading project, Transhumania.

The Gate House

By Nelson DeMille,

Book cover of The Gate House

The Gate House is a sequel to DeMille’s successful novel The Gold Coast, which I really enjoyed. Who wouldn’t like a tale of seduction, betrayal, and violence set about a Mafia don moving into a wealthy WASP enclave on Long Island’s North Shore.

I found The Gate House to be even better. The narrating hero of The Gold Coast returns ten years later. He’s older, wiser, but no less sly, cynical, and funny. His ex-wife is also back, and despite his thinking that she is more than a little crazy (and maybe a bit homicidal), he’s still attracted to her. To top things off, the Mafia don’s son, now himself the don, is looking for vengeance. The Gate House is full of sex, humor, and ultimately, violence. 


Who am I?

As a thriller writer, I have a simple goal: I want to entertain. I'm not the kind of writer whose name is coupled with the Pulitzer Prize or the National Book Award. I write the kind of stories people read to divert themselves on a rainy afternoon or on the beach or on airplanes. My hope is that I can divert and delight my readers. Help them forget the real world for a while. Give them an enjoyable reading break. If people have fun while reading my thrillers, I've done my job.


I wrote...

Murderous Spirit

By Geoff Loftus,

Book cover of Murderous Spirit

What is my book about?

Jack Tyrrell was a burnout. A former Green Beret and U.S. Marshal, he’s become a drunken loser who accepted a bribe and was shot by the people who bribed him. Tyrrell survived. His wife, Maggie, did not. Five years after her death, Maggie appears to him as a ghost and offers him a chance to make things right. She introduces Tyrrell to Harry, who may literally be heaven-sent. Working with Harry, Tyrrell sets out to help a veteran who’s suffering from PTSD and has assassinated a pair of Wall Street CEOs. Action, murdered Wall Street titans, the Russian mafia, and a beautiful woman mix with questions regarding free will and moral behavior to give this thriller a spiritual edge. 

Passage to Juneau

By Jonathan Raban,

Book cover of Passage to Juneau: A Sea and Its Meanings

To my mind, Raban is among the greatest of travel writers whose words so truly mirror the instability of the waters and lives through which he navigates. Here he travels from Seattle to Juneau, focusing his penetrating gaze on the Inside Passage and its inhabitants with the same brutal honesty he turns on himself as his marriage unravels. Alaska and the human condition are portrayed with panache, wit, and the clarity of a photograph. He carries you there with him round every eddy and over every fall. How can anyone write so well, so consistently?


Who am I?

For five years I hitchhiked round the world, for the most part in a kilt. I cycled 5000 miles behind the Iron Curtain before it fell and took a dog team across Alaska. I’ve sailed solo round Ireland and endured storms off Greenland. Currently, I’m cycling in stages from North Cape to Cape Town.  Unconventional travel has been a part of my life for forty years.  As a writer I try to inform and entertain, and my eye is drawn to quirky detail and humour.  I’m inspired by wild places and the people who live in them:  their customs and intrinsic wisdom.  In particular I’m fascinated by the Far North and have travelled extensively throughout this region.


I wrote...

Tracks Across Alaska

By Alastair Scott,

Book cover of Tracks Across Alaska

What is my book about?

‘He arrived in Manley from Scotland with no dogs, no sled, and no experience. As a matter of fact, he’s so green that he calls a sled a sledge.’ This is how a local paper greeted Alastair Scott’s arrival in Alaska. Its cynicism was shared by nearly everyone to whom he announced his intentions: to acquire a dog team, learn the techniques on which his life and that of the dogs would depend, and then travel 800 miles in mid-winter along the line of the Arctic circle. Five months later he defied the cynics and Tracks Across Alaska is his extraordinary account.

Related with great humour and penetrating insight, at its heart, this is an evocation of wilderness Alaska, its history, the plight of its native peoples, and conversations with the state’s diverse inhabitants today: beaver trappers, F15 pilots, Iditarod winners, and recluses from all walks of life. And threaded throughout is the heartfelt bond that holds one man and eight dogs together in a beautiful yet unforgiving environment.

New book lists related to sailboats

All book lists related to sailboats

Bookshelves related to sailboats