Dreamers with a Sense of Humor

Renee D. Petrillo’s sailing memoir, A Sail of Two Idiots, tells the familiar but still irresistible story of a couple who decide to leave the 9-to-5 grind and trade it for life on the water. Published by International Marine in 2012, this 304-page paperback (priced at $12.16 through Amazon at the time of publication) blends candid self-reflection, practical cruising insight and a steady thread of humor. The book’s sub-headline—“100+ lessons and laughs from a non-sailor who quit the rat race, took the helm and sailed to a new life in the Caribbean”—captures its spirit: part how-to, part travelogue, and part laugh-out-loud confessional.

What makes Petrillo’s account useful to readers interested in cruising, liveaboard life, or planning a move to the Caribbean is its balance of aspiration and realism. She chronicles the emotional buildup to the decision to go cruising, the practical considerations in choosing the right boat for bluewater passages and coastal exploration, and the process of creating a flexible itinerary that accommodates both weather and whim. Throughout, she peppers the narrative with lessons learned the hard way—those small, specific moments of failure and recovery that become the most instructive chapters for new sailors.

As a sailing memoir aimed at non-sailors and aspiring cruisers, A Sail of Two Idiots is especially valuable for its plainspoken tone. Petrillo is not trying to dazzle readers with technical jargon; instead, she writes as someone learning in real time, consulting experts when needed and admitting landlubber foolishness when it happens. A standout passage reflects that balance: “It was the best of dreams, it was the worst of dreams, it was an age of consulting the nautical experts, it was the age of landlubber foolishness.” That line sums up the emotional roller coaster of taking on a new lifestyle—equal parts exhilaration and humility.

Readers looking for practical guidance will appreciate the book’s emphasis on concrete topics: how to evaluate a sailboat for liveaboard and cruising suitability, the essentials of provisioning and safety, and how to adjust plans as conditions change. Petrillo’s approach leans toward realism rather than idealism; she offers checklists of considerations rather than rigid prescriptions. For anyone researching sailboat selection, basic seamanship, or the logistics of extended cruising to the Caribbean, her firsthand observations provide a grounded primer that complements more technical sailing manuals.

Equally important is the memoir’s role as a morale booster. Many cruising books focus on either technical instruction or epic adventures. Petrillo’s narrative sits between those poles, offering laughter alongside useful takeaways, and reminding readers that mistakes are part of learning. Her “100+ lessons and laughs” format encourages readers to see the value in incremental progress and resilience—qualities essential for safe and enjoyable cruising.

For SEO-aware readers searching for resources on transitioning to a cruising lifestyle, this book checks several boxes: relatable personal stories, actionable advice on choosing and outfitting a sailboat, and first-person accounts of sailing to and exploring the Caribbean. While not a detailed seamanship textbook, A Sail of Two Idiots functions as a motivational, practical, and entertaining guide for those dreaming of leaving office life for salt air and sailing horizons.

Note: This review appeared in the November 2012 issue and reflects the book as published by International Marine in 2012. Petrillo’s memoir remains a useful starting point for non-sailors and those planning a gradual, laughter-filled transition to cruising life.