What Is Sailboat Chartering?


The Skills | The Cost

To many sailors, sailboat chartering means freedom of sailing in warm, wonderful areas, full of spectacular anchorages, using a nice, well-maintained boat. All true. However, because of many misconceptions, 2 issues should be tackled from the onset: the skills or the necessary experience and the cost of chartering. We will then show you the different types of charters, and how to have the best possible experience.

The Skills

Many times over, I have read in newsgroups on the Internet, or heard from fellow sailors: "My wife and I own and sail an XYZ 28 on Lake Ontario, but we have never chartered in the Caribbean. We have been thinking about this for a long time, but we're not sure we can handle bareboat sailing out on the ocean..."

Well, it certainly is a legitimate question. But the immediate answer is: If you have handled a 28 or 30 footer on a lake or in coastal waters, whether cruising or day-sailing, you can most probably get by safely and successfully in the Caribbean, if you respect the sea environment and comply with obvious seamanship guidelines. However, you will need different skill levels depending on where you plan to charter (read further). And by the way, it is a bad idea to lie about your sailing abilities. Serious charter companies will check you out before they let you leave the dock with a $250,000 boat. Plus, it would probably put you in a situation ultimately endangering your crew and yourself. So don't do it.

If you don't feel too sure of yourself, here are some suggestions:

  • Take a "Bareboat Chartering" course near home. Several reputable companies provide them. Understand this though: those courses will not make a sailor out of you if you have no previous experience. But they will teach you a valuable complement to what you already know.

  • Do a week of sailing school charter. (See below).

  • Ask you charter company to provide you with a "Friendly Skipper" for 2 days to make you acquainted with your boat and the area. It is not free, but it is worth the price.

  • As much as possible, for your first time, try to do the cruise with at least one other experienced sailor, whether it is your wife, significant other, or good buddy. Yes, the Caribbean Sea is beautiful, but the Trade Winds can sometimes blow real hard. Therefore, two pairs of experienced hands are, in our opinion, a minimum to safely handle a 30/32-ft. boat in a completely new environment.

The Cost

The vision of the rich yachtsman seating on his boat deck overlooking a Caribbean sunset evokes the words dollars, millions, out of reach etc. Nothing could be farther from the truth.

Let's use the comparison for a 1-week stay between a comfortable -but not particularly fancy - Caribbean resort and a 46ft. sailing yacht (without crew) in the Virgin Islands, for 3 couples, in high season, usually set between December15 and April 30. The table below does not include air fares, which are the same either way, and is shown per couple, for 3 couples sharing the boat.










Total per couple



Even if only 2 couples would share the boat, it would still come slightly cheaper than the resort. Besides, sailing in complete freedom between islands from one dream anchorage to the next bears, in my view, much more glamour than seating on a beach at a resort.

Keep in mind, however, that you may find slightly lower charter prices than those shown here (source: BVI Yacht Charters 2011). However, in the chartering industry, you will get what you pay for and this is one area where you definitely want quality and service. We will show you how to recognize those 2 elements in our other articles of this section.