GETTING SCHOOLED: Go full tilt in the BVI

Chartered Territory

With our guide to bareboating, it's easier than ever to rent and rule your own sailing ship

Eric Hansen

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I HAVE BECOME—I will admit—a sailing dweeb. Since graduating from my Fast Track to Cruising course, I moor coffee tables to couches and call out nautical commands while grocery shopping (“Cookies alee, prepare to jibe!”). I blame the Offshore Sailing School, in party-rific Tortola, British Virgin Islands. As promised, its ten-day Fast Track program transformed me from mountain-town landlubber to bluewater skipper, certified to charter a bareboat—any ship hired without a crew—up to 50 feet anywhere in the world. Let me say that again: Ten days of instruction and charter companies will hand you the keys to a yacht.

The first three days covered the basics. Our enthusiastic 26-year-old instructor went over rigging, points of sail, and elementary seamanship during lectures and outings on OSS’s custom-built 26-foot daysailers. The most important and reassuring lesson: It’s almost impossible to capsize a larger keelboat, since at least 40 percent of the weight is underwater. Next, along with two other students, I settled into a 49-foot sloop under the tutelage of David Gayton, a salty 54-year-old with a sailing résumé that spans three oceans. While hopping from one island to the next, we practiced the basics—rescues, whipping the huge hull around in tight figure-eights, docking the very expensive boat in very unforgiving concrete slips, and anchoring without damaging fragile reefs. We came to understand the workings of the electric systems and diesel engines and plotted courses that accounted for current and leeway, that inevitable sideways drift.

A thrilling feeling of mastery and humility welled up. On the second-to-last day, we dropped David back at harbor and sailed on alone. We headed downwind five miles to a schooner-turned-bar anchored off an uninhabited island, where I realized that I was hooked—that sailing was in me. I walked over to an attractive woman and introduced myself with perfect ship-to-shore radio protocol: “Sexy Lady, Sexy Lady, Sexy Lady, this is Eric.”

Get Certified

Sailing Annapolis
Sailing Annapolis (GlowImages)


If the bareboating certificate in your hand isn’t all the confidence you need, try one of Sunsail’s flotillas. The trips gather up to 13 chartered yachts and their rookie crews for guided group and independent cruising through the Mediterranean or Caribbean. Each flotilla is also accompanied by a veteran captain who’ll offer instruction and reassurance. About $650 per day for an eight-person boat;

These outfits offer distinct routes to a bareboat cruising certificate, which is what most charter companies require before letting you captain a boat. They also offer training in more advanced skills, like celestial navigation and offshore passage making, that you won’t learn in your bareboat course.


Tortola, BVI, and nine other locations throughout the U.S. and Caribbean

The ten-day Fast Track to Cruising, in Tortola, runs $4,860 from December to July, $3,996 July–October, and $4,117 October–December; includes on-boat meals and private accommodations(on-boat and off);


Alameda and Sausalito, California

Club Nautique recently won U.S. Sailing’s Prosser award for outstanding instruction, especially impressive considering the challenges of operating in San Francisco Bay. Its cumulative eight-day Skipper’s Course and four-day bareboat-certification course teach you how to navigate fog, busy shipping lanes, strong currents, and 25-knot winds. Both courses, $2,590, including on-boat accommodations;


Annapolis, Maryland

America’s oldest sailing school offers a progression of three five-day courses, affording apprentice skippers time to explore Chesapeake Bay. All three, $3,240 (April–October only), including accommodations;

Now, Sail the World

Grenadines Palm Island
Grenadine Delight (PhotoDisc)


Itching to buy? Beware. Boat stands for “Bring on Another Thousand.” Purchase programs—leasing your boat to a charter company—help control the costs. You buy a new boat and let a charter company rent it up to ten months each year. In exchange, the company maintains and moors it, and pays you a fixed income (which can often cover your mortgage). Finally, many contracts give you points to spend on other boats in the company’s fleet around the globe. Run the numbers at and

A bareboat should range from $400 to $700 per day, depending on model and season. Stock the galley, step aboard, and sail away. If anything important breaks, your charter company will send someone out from their local base to fix it. Even better: You don’t have to worry about cleaning when you’re done.

Though your bareboat-cruising certificate lets you charter anywhere, be realistic—just because you’ve taken driver’s ed doesn’t mean you’re ready for the Autobahn. The following spots are ordered from easy to hard.

British Virgin Islands

The most popular charter hub in the world offers steady winds and easy navigation between islands. The Moorings,

Sea of Cortez

Spring off Baja’s east coast equals barking seals, flat seas, and crimson sunsets. The Moorings,

Newport, Rhode Island

A reliable summer breeze connects the mainland to Block Island and Martha’s Vineyard. Bareboat Sailing Charters,


Long open-ocean passages (eight miles and more) between lonely sandboxes are an any-season favorite among ambitious sailors. TMM Yacht Charters,

Anacortes, Washington

Summer is the best time to master the fast currents and choppy seas of the San Juan Islands, at the edge of the Pacific. Anacortes Yacht Charters,