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Cruise Control

When not at the helm of HD Brown Enterprises in Ontario, Douglas Brown is likely to be found steering-literally-a very …

When not at the helm of HD Brown Enterprises in Ontario, Douglas Brown is likely to be found steering-literally-a very different ship. Last spring, he captained a 47-foot catamaran to island-hop in the Caribbean with his family. A few months later, he toured the Greek Isles at the wheel of a 39-foot Beneteau yacht with his wife, Sandee, in the self-described role of hood ornament.

With phrases like “trimming the sails,” “running 20 knot winds,” and “heeling 20 degrees” peppering his reports on these excursions, Brown sounds every bit the seasoned seafarer. Not so, says the 51-year-old, who credits an intensive sailing class for his competence and comfort-level on deck today.

“Before Sandee and I took the course, I knew very little,” he says. “By the time we finished, we were able to rent a 36-foot catamaran and cruise the North Channel [in Canada] for eight days on our own.”

The course the Browns took was a 10-day immersion learning program in the British Virgin Islands called “Fast Track to Cruising” intended to ready even the novice sailor for a “bareboat cruise,” or chartering a boat without a captain or crew. Offered by the Offshore Sailing School, the course begins with four days of two-hour classroom lessons followed by sailing excursions during which would-be skippers put basic theory into practice on board a Colgate 26, a tiller-driven keelboat specially designed for training. Not only do class members handle the boat on the water, they ready the boat for sail, stow provisions, plot a course, and learn about safety procedures and sailing etiquette on the water. Once competent with terminology, the techniques of tacking (changing direction), jibbing (stopping), and the finer points of sailing protocol, participants step up to a 46-foot yacht where they will live-and learn-during the final six days of the course.

“There you cover basic navigation, plotting a chart from a GPS, and heavy weather techniques,” says Diana Smith, a spokesperson for Offshore Sailing. “In addition to learning how to handle the larger boat under sail, you practice maneuvering in close quarters and how to operate its onboard systems, including the head, the galley, the diesel engine, electrical systems-all things you need to know for a bareboat charter.”

One of the trickier exercises is a man-overboard drill, involving the rescue of a dummy dubbed Bob. “It’s disconcerting because you have to sail away first to give yourself room to circle back around,” says Brown, who spends his time off of the water as president of a privately owned Canadian auto parts and sports equipment company. “Then you need to come up directly into the wind in such a way that the boat will coast to a stop right alongside him.”

While Brown hasn’t had to reenact that lesson in his subsequent bareboat adventures, he did have a few uncomfortable moments at the helm of the catamaran in Greece. Crossing a narrow channel in a light wind, the boat glided past a mountain and-whoosh-the wind whipped through at 35 knots and pushed the boat onto its side. “It gave me a fright, and I put the boat up to the wind faster than I should have,” recounts Brown. “We went from heeling 20 degrees on one side to heeling 20 degrees on the other.”

While momentarily sobering, the experience brings to the forefront one of the things Brown most enjoys about sailing. “You have to think about and adjust to what is happening all the time-changes in the wind, the current,” he explains. “It’s a mental challenge.”

Next on the Brown family sailing excursion itinerary is a trip to Norway to see the midnight sun. That plan is one reason that Brown recently went back for a refresher and skill-sharpening course, this time with his daughter, Sarah, in tow. The pair headed to the Offshore Sailing’s facility in Captiva Island, Fla., where Sarah focused on the basics of learning to sail while Brown honed his navigation skills. After four days, the duo left for a more intensive live-aboard lesson in the Bahamas.

Coursework isn’t all anxiety-inducing drills, certification test preparation and vocabulary tests. After all, sea voyagers must also practice the art of boat-side snorkeling and swimming, lunching al fresco on deck and sailing into a harbor at sunset bound for a meal ashore. They also log ample time simply gliding through the turquoise blue waters, sails filled with wind, heading for exotic ports of call. Offshore Sailing’s British Virgin Islands course, for example, might include anchorage at Cooper Island, Virgin Gorda, Anegada and Norman Island. And, finally, on graduation day, sailing students leave their instructor on shore and test their new skills during a 24-hour mini-cruise on their own-a key part of the experience for Sarah, who plans a bareboat charter with a friend this summer. To Brown, who did his own first bareboat charter less than six months after completing the Fast Track course, that independence is what it’s all about.

“It offers tremendous freedom,” he says. “On a cruise you stop at the major harbors, but with a charter you can anchor anyplace you want-see tiny beautiful islands-and change your course as you go.” 


Already, there are 11 million recreational sailors in the United States, and each year another 600,000 new sailors take to the water. Among these growing ranks of “yachties,” bareboat hire-easier and less costly than owning a yacht-is becoming increasingly popular.

And for good reason. As the old adages go, “a boat is a hole in the water into which you dump money,” and “BOAT is an acronym that stands for Bring Over Another Thousand.” Renting one, on the other hand, is a hassle-free way to enjoy the pleasures of yachting without the costs of maintenance and repair, insurance, berthing and crewed transportation between ports.

Surprisingly, no formal certification is required to charter a boat. That said, most chartering companies grill clients on their sailing experience to gauge their skill level. Those found wanting will be urged to take a captain along or to go the crewed yacht charter route. Some chartering companies, such as The Moorings, offer a middle ground-an experienced skipper accompanies you on day one to acquaint you with your boat and the local waters.

Flotilla sailing is another great option for first-timers. In a flotilla, you charter and have full responsibility for your boat, but tour with between eight and 10 other yachts, including a lead boat with an experienced skipper at the helm. Each day, the lead boat’s skipper sets a course and offers a briefing on the weather conditions and any navigational hurdles, such as hidden reefs, along the way. After that, you’re on your own until the flotilla regroups at the evening’s destination-but with the reassuring knowledge that the skipper and his crew are nearby and on-call to provide any advice or help you might need.

What to Expect

“Bareboat” is something of a misnomer. Ice, fuel, water and linens are standards, but amenities such as snorkeling gear, barbecue grills and GPS are often included. Be sure to check with the charter company about what else comes with your boat-and what they recommend you bring along.

Where to Go

For your first charter, choose carefully. In general, you’re looking for a destination with sheltered inlets, steady trade winds, and clear water relatively free of navigational hazards, such as the hidden reefs, blustery winds and strong currents of the Greek Isles. Doug Brown suggests the British Virgin Islands as a beginner’s first sail destination. “The winds are predictable and the water is clear, so you can avoid reefs,” he explains. “The islands are beautiful and relatively close together, so you navigate and make stops during the day easily.”

About Jennifer Pellet

As editor-at-large at Chief Executive magazine, Jennifer Pellet writes feature stories and CEO roundtable coverage and also edits various sections of the publication.