Finding Serendipity
An Adventure of Boating on North America's Great Loop
John Gray traces his Great Loop journey through the backyard waterways of America, from rivers and canals to the communities and characters that made the trip unforgettable.
The Great Loop draws people in for all kinds of reasons, and John Gray captures the pull of it well: the idea that more people have climbed Everest than completed this route, yet it runs through protected rivers, sounds, canals, and lakes rather than mountain wilderness. This is an accessible adventure, and that accessibility is part of what makes it so compelling.
Gray writes in an easy, approachable style that takes you along on the water rather than lecturing you about it. The focus is on the experience: the towns and cities the Loop passes through, the history baked into the route, and the community of fellow loopers you meet along the way. For anyone in the dreaming or planning stage, it delivers both inspiration and a realistic sense of what the journey actually feels like day to day.
If you are trying to convince a skeptical spouse or partner, or just need a nudge to stop planning and start moving, this one works well for that.
Thoughts from a Looper:
There’s something John Gray mentions that stopped me: more people have climbed Everest than have completed the Great Loop. And yet this route runs through protected rivers, canals, sounds, and lakes — not mountain wilderness. It’s an audacious journey hiding in plain sight, tucked into the backyard waterways of a continent most people have never seen from the water.
What readers consistently say about this book is that it puts you right there alongside John and his wife Laurie… not as an observer, but as a stowaway. Gray writes about the experience of actually being on the water: the towns, the history, the characters, the daily rhythm of locks and fuel stops and new anchorages. It’s less a how-to guide and more a honest account of what it feels like to put all that planning into practice.
One thing worth knowing going in: this book doesn’t skip the unglamorous parts. Some readers find the middle stretch — lots of locks, repetitive days, pushing through less scenic sections — a bit of a slog. Others find that honesty to be exactly the point. The Loop isn’t all turquoise water and perfect sunsets, and a book that acknowledges that is doing you a favor.
If you’re still deciding whether the Loop is right for you, or trying to figure out what version of it fits your life, this one is worth your time.
Why We Read It in the Great Loop Book Club
A member of our community was already reading it and passed along the recommendation. And once we looked into it, the timing felt right for May.
Finding Serendipity works well for where a lot of our members are right now: curious, drawn to the Loop, but still working out what it would actually look like for them. Gray doesn’t oversell the journey or leave out the hard parts, which makes this a more honest read than a lot of Loop memoirs. You come away with a clearer sense of what the day-to-day really feels like — the locks, the planning, the community, the tradeoffs — and that kind of clarity is genuinely useful whether you’re still dreaming or starting to make real decisions.
It’s also a good one to share. Several readers have mentioned passing it along to a spouse or partner who needed a little convincing. If that’s where you are, you’ll know by the end of chapter one whether it’s working.
As an Amazon Associate, I earn from qualifying purchases at no extra cost to you.