Bareboat racing is very popular, and maybe you have heard of it, though not sure what it is. The word bareboat really does not describe much in ways of what it is, especially if you do not know that much about sailing.

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“Does ‘bareboat’ mean there’s nothing on the boat?”


Bareboating is the act of chartering a sailboat that one lives upon, navigates, and operates for a vacation. To charter a sailboat, one must usually be able to demonstrate boat handling skills especially in operating the boat under power, docking, and anchoring. Typical sizes for bareboats come in the range of 30 ft. to usually about 60 ft. at the upper end. Most charter operators require a sailing resume listing sailing experience, boats that one has sailed and operated, and navigation and racing experience.

For many sailors, racing a bareboat is a means of sampling something bigger, nicer and newer than their boat at home.

Bareboat racing is a new twist on bareboat chartering. Bareboat racing is chartering a sailboat for one reason, and that is racing. There are bareboat races all around the world now.

Bareboat chartering

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To charter a sailboat, you just don’t give them some money, show them some identification and it is yours. Remember in bareboat chartering, you are the captain, and your spouses and friends are the crew. means that you and your crew are fully responsible for safely operating the boat and navigating successfully in unfamiliar waters. Meeting these new challenges will improve your skills. Along with the responsibilities entailed on a bareboat charter comes unlimited freedom—freedom to do exactly as you wish, when you wish, how you wish. Bareboating is like owning a boat for a week, with all the joys and agonies that ownership entails.

If you are a boat owner or sailor who has coastal sailing experience on boats comparable to the one you are chartering, you should have no problem in most sailing areas. For the potential skipper, companies ask for a sailing résumé (it pays to be truthful about your experience); in some areas, a U.S. Coast Guard captain’s license or a certificate from a reputable bareboat sailing or skippering course are required. You should be familiar with basic boat handling procedures (including docking and anchoring), know the rules of the road, and be familiar with basic seamanship, navigation, and piloting.

Fifty years ago, the only way a sailor with some adventure in them could see the world under sail was to stash away some cash, buy a boat, outfit it for ocean voyaging, sever his shoreside connections, hoist the sails, and go. Could be very very expensive.

All that began to change in the mid to late 1960s when Jack Van Ost started Caribbean Sailing Yachts (CSY) on Tortola, in the British Virgin Islands. By the 1970s, Van Ost and CSY had expanded down island to St. Vincent. Also jumping in to the charter game on Tortola were Charlie and Ginny Carey, who in 1969 started a company called The Moorings. Their fledgling business, providing qualified clients with clean, well-equipped boats for rent without skippers or crew, helped ignite an industry that today puts the dreams of faraway ports at the fingertips of sailors all over the world.

Best way to be assured a charter

Get certified

One of the ways to do this is go through American Sailing Association. The American Sailing Association was founded in 1983 with a simply stated mission: to teach people to sail safely and confidently. To achieve that goal, the ASA set out to establish standards against which to measure a sailor’s level of knowledge and skill, the first such unified standards in the U.S. to apply to sailors in keelboats. Today, the ASA is an association of sailing schools, charter companies, professional sailing instructors, and sailors, with over 300 affiliated sailing schools located throughout the U.S., as well as in Europe, Japan, Central America, Taiwan, China, and other far eastern countries. These accredited schools offer ASA certification to individuals who meet the requirements for a given level. To date ASA schools have certified nearly half a million sailors!

The ASA system has eight primary levels of student certification from Basic Keelboat all the way to Offshore Passage making. Whether your goal is to skipper a bareboat charter in the Caribbean or to crew confidently on a short weekend sail, the ASA’s sailing-education system will guide you as you learn the theory behind sailing, practice the skills needed to handle a sailboat, and build the foundation of knowledge that will enable you to navigate a vessel safely and within the law.

Examples of certification

Basic Keelboating Sailing

Basic Coastal Cruising

Bareboat Cruising

Coastal Navigation

Advanced Coastal Cruising

Basic Small Boat Sailing

And many others.

Don’t think these are not fun. On almost certification courses the training is very enjoyable, with a lot of information and hands on. On many, you can even take a vacation sailing and get certified.

Some sailboat chartering companies are Windsong, Sunsail, the Moorings, and many, many others.

Bareboat racing

Many bareboat companies organize race weeks. Teams get together and rent a specific type of boat, each day another leg is raced from one perfect anchorage to the next. You don’t have to be good to enter, just willing. Many are super keen and the top place getters are cut throat. Many though don’t really care where they come, its more about the comradery. All the boats are exactly the same, so competition is close. No spinnaker or poles are allowed. Some of these races go from country to country.

If you have had the inkling to sail the great wide blue, and race, without the headaches of ownership, bareboating is a blast, relaxing, and gives you a level of confidence you will not find in other activities.

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