Sailor Profile: Chris Doyle

Over years of cruising and chartering in the region with Chris Doyle’s books as my inspiration, I’d often wondered, How does he do it?
Chris Doyle
Prolific cruising-guide author Chris Doyle has been covering the eastern Caribbean since the 1970s. These days, he heads to the islands each winter aboard his catamaran, Ti Kanot, to keep the guides up-to-date. CWD

Picture this: You’re cruising or chartering in the Caribbean. You’ve made landfall at a new destination in the Windwards or Leewards. The sails are furled, and the anchor’s down. From the cockpit, you take in lush tropical surroundings.

Now what?

Chances are, if you hadn’t already done so during your passage, you pull out one of the spiral-bound island guides by author Chris Doyle. For decades, Doyle has consistently provided updated and practical advice — navigational and après-­navigational — on every nook and cranny of these tropical cruising grounds.


Here’s a hike and a fort with a sweeping view. There’s a chandlery for the impeller or fuel filter you need. And that’s the name of a decent breakfast place you can plot on your land course back to the boat.

Over years of cruising and chartering in the region with his books as my inspiration, I’d often wondered, How does he do it? Doyle isn’t the only one out there making guidebooks for mariners. But in this part of the Caribbean, he’s certainly distinguished himself as the first, notwithstanding the longtime undisputed presence of Donald M. Street Jr., whose focus is on sailing directions.

I got my answer during a summer visit to landlocked Vermont. In Corinth, a hamlet whose sloping green hills are a fine hurricane hole for a sailor on the run from the threat of storm, Doyle, an energetic 74, scoured his memory to reconstruct the genesis of what has become his life’s work.


In his late 20s, as a skipper in the islands who was active in the early charter trade, necessity was his mother of invention. Feckless vacation sailors would get ahold of Street’s guides and, too inexperienced to understand them, would go aground. That was hardly the entire problem.

“In the early days of bareboat chartering, as today, you’d have the chart briefing, where you’d spend time with the base staff going through every anchorage in the itinerary,” he says. “There’s no way customers would remember everything they were told. So my first cruising guide was a photocopied chart with notes. Big notes and lines and things.”

Charter companies borrowed Doyle’s crib sheets, and by the time he was skippering Gulfstar 50s for Stevens Yachts in the 1970s in Grenada, he was asked to create the Stevens Cruising Guide. By now, Doyle was acquiring a reputation, and it got complicated.


“Every time I went ashore, people would say, ‘Where can I find this? Where can I find that?’ It was becoming a pain in the neck to answer all these people,” he says.

Time passed, Doyle left Stevens to charter on his own, yet the curious and clueless still found him.

“Most cruisers hang out for weeks in one port. I’m in one day and out the next”

“I was complaining about having to answer all these questions to a guy named George at a party on a boat in Bequia,” Doyle recalls. “He said, ‘Why don’t you write a book?’ So I did. I had no idea how to write or publish a book. I started getting the information together and writing it and approached a publisher or two, and no one wanted to know anything about it.”


Undeterred, Doyle, while living aboard, charged ahead, surveying, reporting, writing, illustrating and financing — by also selling advertising — what became the first Windward Islands guide. He hired a printer in Barbados to produce it, and wound up with a bill more than twice as big as he expected.

This led to a marketing-and-­distribution method that, by today’s standards, could only be termed ground-drone delivery. After transporting the books back with him aboard his own sailboat to the Windwards, he set out to make a buck from them to offset his debt.

“I used to be quite good at windsurfing,” he says, “so I put a backpack of books on my back, and I windsurfed from boat to boat and sold them. The first print run was 5,000 books. Each book cost $5.”

At that price, the 1980 guide, while popular, was losing money, and he kept it afloat by working as a charter skipper. Then came a boost.

“It became important to charter companies to have these guides,” he says. “Simon Scott, then vice president of The Moorings, bought a thousand books. Simon and his wife, Nancy, had done the guide to the Virgin Islands around the time I started my Windwards guide. They contacted me and asked if we could work together. And we have been ever since, to some extent.”

Indeed, the Scotts, who’d put together a cruising guide to the U.S. and British Virgin Islands while they were liveaboard sailors, had attracted an audience similar to Doyle’s. When Simon joined The Moorings in the early 1980s, Nancy continued to oversee publication of the guides under the business name Cruising Guide Publications. His position at The Moorings (he rose to CEO, then left the company in 1997) made it possible for him to see the guides in a strategic light, much to Doyle’s — and his — ultimate good fortune. Since Scott’s tenure, the guides are standard issue aboard Moorings charter boats.

windward islands guide
Doyle’s first book, a guide to the Windward Islands in the Caribbean. CWD

Today, while the Scotts edit, publish and distribute Doyle’s guides, their own and others, Doyle himself returns to the Caribbean every winter to update his work from aboard his catamaran, Ti Kanot. He and the Scotts have also brought their products into the electronic age, with GPS coordinates, downloadable versions, and online updates and corrections.

Doyle credits his audience with helping him stay current.

“We’re constantly in a state of revision,” he says. “When you have to cover a large territory in a short period of time, it’s always good to find someone who really knows the area to point you in the right direction.” Yes, but still — how does he manage to get to every anchorage?

“I just do it,” Doyle says. “Most cruisers hang out for weeks in one port. I’m in one day and out the next, depending on the size of the place. Maybe a week in English Harbour, Antigua. Someplace like Nevis, I’m there two days.” No doubt, the authors and publishers have contributed to the popularity of the eastern Caribbean as a sailing destination.

“They’ve allowed a lot of people to cruise who could never have cruised before,” Doyle says. “Our guides help people to find anchorages that they might not otherwise find. We do popularize things, and that can make places a little more crowded than they might otherwise be. But I think it’s all right.”

And while he faithfully continues to visit every port aboard Ti Kanot, discovering new hideaways, dropping lead lines and drawing large-scale illustrations of anchorages, there’s one chore he no longer handles. “I’m not selling ads anymore. That is the job I hated. I am not a good salesman.”

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Elaine Lembo is a CW editor at large.