Under a Cloud of Sails

Memoirs of a Free Spirit

Non-Fiction - Memoir
344 Pages
Reviewed on 09/29/2020
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    Book Review

Reviewed by Asher Syed for Readers' Favorite

Under a Cloud of Sails by Winston “Win” Williams is the author's memoir chronicling a roller coaster ride of a life with literal highs and devastating lows. Williams begins with a background of his childhood and transitions into teen years where a summer in Nantucket creates the springboard that launches a lifelong passion for sailing. Williams becomes more and more entrenched in sailing life and his experiences on and below deck, and through both remote and known territories, give rise to some extraordinary ordeals. The discovery of the anchor of the HMS Bounty, quarantine, the loss of crewmembers, crocodiles, isolated tribes, and a potential entanglement with kidnapped children are just the tip of the iceberg. Before the age of thirty, he is captaining a schooner, but his trajectory is almost immediately halted for decades as he marries a much younger Filipina in Manila, becomes a father, and then falls into a pattern of addiction that derails his life in its near entirety.

Winston Williams has certainly lived in a way worthy of a memoir and Under a Cloud of Sails does well in documenting the intricacies of a man who seems to always be in pursuit of something larger. Where the first part of the book zones in on his youth, the latter half offers a full immersion into the psyche of a usually but not always functioning alcoholic. For me, the most poignant part of Williams' story is the moment he finally accepts he has an addiction that will require a firm intervention. Imagining a man who has weathered squalls sitting on the floor, destroyed by an entirely different type of drenching, was not easy to read. Still, it is Williams' raw honesty and recognition that allows us to see how his journey toward sobriety was hard-won. To go from captaining a vessel to mopping a church floor and not granting shame the opportunity to shake him is a testament to his humility. I am reminded of a quote by Austin O'Malley on the mindfulness of humility: “The gale that breaks the pine does not bruise the violet.” Williams has in his life been both the pine and the violet, but it is his reconnection with his children, his acceptance of who he is and what he's done, and his confidence to get back up and pursue a dream once more that makes this book more than just a travel memoir.