By Bob Payne

Here’s a secret about learning to sail: It’s easier to master sailing on a larger boat, such as you'd typically charter, than on a smaller one. On a larger boat, everything happens more slowly, and mistakes (short of running down a Coast Guard cutter) are more easily forgiven.

Can You Handle It?
Despite what you’ve seen in the America’s Cup races, your time aboard a charter boat is not going to require too much. For the most part, you’ll hoist the sail in the morning, take it down in the evening, and the rest of the time simply tinker with winches, cranks, and pulleys to maintain course. Some upper body strength is recommended, however, because hoisting will require some leverage.

More important than brute strength, sailing requires a modest understanding of mechanics: Enough to figure out what to do if, say, the head (that’s nautical for bathroom) gets plugged. You need not be a champion swimmer, but if motion sickness or claustrophobia plagues you, reconsider a dryer destination. Plan to be in constant motion, and live in quarters that are a bit tight.

Essential Skills
If you want to charter a bareboat--in other words, a Hertz-style rental in which you do your own driving--the best way to learn is by sailing in home waters. Most sailing schools offer a course in bareboat cruising, though typically they require a basic course or two, at $300 to $400 per, before advancing you to a bareboat certification course, which will run anywhere from $300 to $600 more. Another option is an all-inclusive live-aboard package. Taking a week to 10 days and costing $1,500 to $3,000 including certification, the learning process can be a sailing vacation in itself.

Both U.S. Sailing (401-683-0800) and the American Sailing Association (310-822-7171) offer certification, but in most parts of the world no license is required to charter a bareboat. Instead, what charter companies care about most is experience. They’ll look closely at your sailing résumé and often put someone aboard for a few hours to evaluate your skills. If your abilities pass muster, you can head out on your own. But if you should call the chart a map or crash into the dock so hard that you wipe out somebody who is walking by, they'll probably insist you take a skipper along, at your expense (generally $100 to $150 per day).

Ironically, it’s often not the "pure" sailing skills that are most important on a sailing vacation. It’s the ability to maneuver the boat under power into a crowded area and anchor it in a way that will let you and your neighbors get a good night's sleep. That, as well as being able to recognize whether that interesting bird just ahead is floating serenely on the sea or if it’s standing in just three inches of water.

Gear Up
Most bareboats are anything but bare, so the gear you need to bring is minimal: sunscreen, two pairs of polarized sunglasses (in case one goes overboard), a sun hat, foul-weather gear, and nonslip deck shoes. Many sailors also bring a hand-held global positioning system (GPS) device. In the context of sailing, they’re relatively inexpensive and can save you the embarrassment of pulling into St. Thomas expecting to find Tortola.

Speak the Language
The vocabulary of sailing is vast, much of it making no sense to the uninitiated. You do have to learn enough of it, though, to convince the charter companies that you speak their language. The six words you'll probably find most useful, other than "Can you give us a tow?" are:

Port: The left side of the boat when you are facing forward. Not to be confused with port, as in harbor, porthole, or a sweet after-dinner wine produced in Portugal.

Starboard: The right side of the boat when you are facing forward. Not to be confused with port, as will happen if you are facing backwards.

Tack: Another multifaceted word, most often used to describe shifting the sails from one side of the boat to the other when headed upwind.

Jibe: A similar motion to tacking, except that it occurs when sailing with the wind behind you. If uncontrolled, it can be violent and result in the loss of hats, sunglasses, the mast, and even consciousness.

Boom: A horizontal bar along the bottom of a sail to give it support. During an uncontrolled jibe, it is the source of the violence mentioned above.

Sheet: A line used to control the sails. When somebody yells "Sheet, Sheet," they are telling you to pull in the sheet as fast as you can (and not, for the record, uttering an expletive with a Spanish accent).

Bob Payne has sailed most of the way around the world. He has been a contributing editor of Sail magazine for 20 years, a contributing editor for Condé Nast Traveler, and a frequent contributor to Outside. Twice a month Bob treats iExplore readers to insights and advice from his latest journeys in his column "i on Adventure."