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From Away.com

A Sailing Primer
Sail through the planning of a windswept vacation

By Paul McMenamin

Windjammers or catamarans, intrepid explorer or relaxed passenger: there are as many options to sailing as there are waters and harbors to set anchor. The first choice: decide if you want to charter a crewed ship or skipper your own boat (also known as bareboating). This will set the course of the rest of your sailing adventure.

Crewed Charters
If you want to recapture the romance of the age of sail while letting a skilled crew do all the work (including the preparation of gourmet meals), we recommend a windjammer or tall ship vacation. Windjammer and tall ship cruises are available worldwide, from the snug harbors of Maine to the tropical islands of the South Pacific.



Selecting a great crewed charter is a challenge. With bareboat operators, company size generally assures a certain level of quality and service. However, some of the best crewed charter operations are small, perhaps just a husband-and-wife team. And finding a top-flight small operator isn't easy, since the good ones don't need to advertise—they get all the business they can handle from word of mouth. It is essential to get the advice of a reputable charter broker.

While a 34-to-40-foot yacht is ideal for a two-couple bareboat vacation, we prefer crewed charters in the 50-to-70-foot range. With a yacht of this size, three couples can each have a private cabin, there will be a full-time cook aboard, and the vessel can easily carry fishing tackle, dive gear, and windsurfers without compromising deck space.

Self-manned Bareboat Charters
Bareboating is generally the least expensive and most liberating kind of sailing holiday. You're free to plan your own itinerary, sailing when the wind is good, relaxing along a deserted beach when you want a break. While operating a large yacht is not child's play, most people with some keelboat experience will be able to charter in a destination like the Virgin Islands, although you may have to put a skipper on board for the first day or two.

Bareboat Certification
If you've never bareboated before, it's a good idea to take a bareboat certification course. While earning your bareboat certificate will not guarantee that you will be allowed to charter on your own (you must still prove your skill to the charter company), a bareboat course is a logical start. At present, there is no standardized curriculum for bareboat certification, and the courses available range from superb to superficial. A good program will span a couple of weekends and include an offshore cruise. You will be trained in sail handling, anchoring, coastal navigation, radio etiquette, emergency procedures, and boat maintenance and repair. A basic bareboat course will train you to operate a boat up to 30 feet. After chartering a 30-footer two or three times, you may want to pursue your advanced bareboat certificate, which covers yachts up to 50 feet overall.

Below are the most important factors to consider before you book any bareboat trip. Attention to these details will help you avoid the most common problems bareboaters encounter.

Bareboat Considerations
  • Choose a charterer with a proven track record.
    Look for a bonded company that has been in business for at least ten years. Although longevity is no guarantee of quality, you will avoid the typical problems associated with start-ups.

  • Ask about the age and condition of the yachts.
    Pick a company that can give you a boat under five years old, if at all possible. Bareboats take a lot of abuse, and a craft can become a real headache after just a few seasons of use. You'll generally get a better quality boat by chartering early in the season, or soon after the new boats have been delivered. Caribbean boats, for example, are likely to be in much better shape in December than in March.

  • Learn the hidden costs in advance.
    Know what you'll be spending before you set sail. Your bareboat fee typically omits provisioning, charter taxes, land accommodations, and extras such as windsurfers or dive gear. You may even have to pay extra for insurance—an absolute necessity.

  • Go for the "extras" package.
    Most charter companies offer a package for a flat fee that includes windsurfers, inflatable dinghies, and other fun items that are usually well worth the investment. Once you've started your cruise you won't want to backtrack to the charter base to upgrade your accessories.

  • Find out what qualifications are required.
    Almost all charter companies will ask you to provide a sailing resume establishing that you have previous experience on a yacht of the size you plan to charter. Having a bareboat certificate helps, but this is no guarantee that you'll be allowed to charter on your own. When you arrive in your destination, you'll be checked out on the water, and a skipper will be put on board if necessary.

  • Find out the best season to sail.
    Just because you pay high season prices doesn't mean conditions will be ideal. Ask about wind, weather, and water temperatures before you go. In many parts of the Caribbean, for example, the best sailing is in the late spring when prices are much lower and the anchorages are far less crowded.

  • Ask for references from past customers.
    Before you put down a deposit, talk to customers who recently chartered the same type of yacht in the same area. You will learn vital facts no brochure would reveal.

  • Don't be too cheap.
    Seasonal discounts notwithstanding, you generally get what you pay for when bareboating. Don't be overly swayed by low prices—saving a few dollars can result in a miserable vacation if your boat is a lemon




Paul McMenamin is the author, editor, and photo director of the original Ultimate Adventure Sourcebook.