The most recommended sailing books

Love with a Chance of Drowning had been recommended to me for a while, but I only recently dove in.

One of the reasons was the high price for the eBook, undoubtedly because this is a traditionally published memoir. And, what can I say? I adored this well-crafted love story set on a small sailboat crossing the Pacific Ocean, sprinkled with fearful and heartfelt incidents.

Torre is a fabulous writer, who pulls you into the narrative. She is witty, sarcastic, smart, straightforward, and doesn’t shy away from sharing personal insights, flaws, and brutal honesty, a touted aspect of my book as well.

The author used the present tense to impart a sense of urgency (it’s a wonderful tool to keep you turning the pages) and focused on the connection, strength, and commitment that is needed to rescue her relationship. This is one of the most skillfully written and compelling… show more.

If The Twilight Zone Companion was my original bible, then the Deep Space Nine Companion was its extensively expanded new testament. The alpha and omega for what a book about the making of a television show could be, this massive compendium was made possible by the unparalleled access the authors had to everyone as the show was in production. This book blew my mind with all the details it included and all of the aspects examined. Simply a treasure for all Star Trek: Deep Space Nine fans. That said, this is an authorized book, meaning nothing was published without the studio’s oversight, which differentiates it from the earlier books on this list. Nonetheless, it’s the one I strove to match when I compiled my own study on the making of Gene Roddenberry’s Andromeda entitled Sailing the Slipstream (a book I plan to re-format and re-release in an anniversary edition). 

When I read this it felt like a seagoing version of One Hundred Years of Solitude, and it was touch and go which to include in this list. But if you’re like me, and love the sea, there’s no real choice.

In this epic novel we’re shown how the Danish port town of Marstal – and people who call it home – evolve over the course of a century. The novel brilliantly captures the pull that the sea has over the town’s inhabitants, and their struggle to keep what makes them human when faced with its power and scale.

There’s a fantastical element too, just a touch here and there, which somehow matches how most of us experience the unexplainable.  

Before the Holy Roman Empire, there was Byzantium. Prior to better-known names like Charlemagne or Thomas Aquinas, there were men like Justinian, who codified Roman law for posterity, or Photius the Great, who gave concise theological treatises to eager audiences of the highly literate populace of Asia Minor. Wells explores the heart of Roman civilization in the Eastern Mediterranean where the flourishing Byzantine Empire preserved ancient learning. Sailing from Byzantium investigates the historical and geographic forces at play which eventually made Byzantium a "forgotten" empire, yet which today—whether it's acknowledged or not—has left its indelible mark on the modern world in remarkable ways. This is not just a journey into history, but an intellectual pilgrimage into the time and setting of almost forgotten intellectual and spiritual giants. 

When I cruised the Bahamas in 1968/69, there was no other book of its kind available. At the time, there was no such thing as GPS, digital, computers and all the other navigational aids to help small boaters today. It was foolhardy to cruise the Bahamas at night and even during the day without local knowledge.

This book provided much-needed navigational directions, headings, and descriptive aids for entrances through coral reefs and harbors, the location of navigational aids, and basic information about each major island.

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. 

Richard Bode’s pocket-sized memoir was given to me by a college friend, shortly after our graduation (as I write this, that was about three decades ago, and I still have this little book on my shelf within reach). It’s got water and sailing (both of which I love), but more importantly, it’s also chock-full of life lessons—without being preachy or overbearing. In the end, you realize that you can plot your own course, adapt to the shifts of wind and waves (Bode’s metaphor for life), and become your own hero.

The first time I read this book I was sailing through the Frisian Islands, where it takes place—though unlike its two main characters, I didn’t have to worry about German patrols or being arrested as a spy. A classic thriller, the remote and shifting islands of the area help to drive the plot. It could, quite simply, take place nowhere else. Great sailing scenes as well!

Bill Tilman was a war hero and an accomplished Himalayan climber – reaching 27,000 feet on Everest without oxygen in 1938 – who turned in later life to sailing as a means of accessing obscure mountain ranges. In 1956 he sailed his Bristol Channel pilot cutter (Mischief) from England to the Chilean channels and made the first successful crossing of the Patagonian ice cap. Tilman was likely not easy to get on with – he tolerates no women on board, and on this particular cruise we never learn the first name of his deputy – but his writing is erudite and amusingly self-deprecating. This narrative concludes with the dry comment: “Ships are all right – it's the men in them.” Tilman sailed to the very end. He disappeared at sea in 1977, in his eightieth year, en route to climb a remote island peak in Antarctica. Would that… show more.

While I enjoyed reading One Girl One Dream and have unconventional ideas like the author, I’m torn about a child sailing the world instead of going to school.

Laura sailed single-handedly around the world when she was 14, finishing at 16. This fascinating achievement made her the youngest circumnavigator in the world. 

The first chapter is a page turner; the subsequent ones are written like a diary. I am usually not a fan of this style, but because her story remains an exciting and courageous feat from beginning to end, it kept me wanting to learn more. It was also fun to read Dutch words and traditions, because I grew up in Belgium. 

I wouldn’t call Laura’s memoir a high-quality narrative or good writing, but it held my attention and that means something for this picky reader.