Bareboat means that you charter the boat and is responsible for operating it and everything else while it is in your care. For experienced sailors, this is the best charter option around – you have complete freedom to go where you want and do whatever you want to do at your own leisure.  If your sailing skills are a bit rusty, there are yacht charter companies that offer a skipper for the first few days of your trip, to help you brush up on your skills and get to know the boat. When you and they feel you’re ready, you’re off on your own.

Most yacht charter companies around the world require you to provide them with proof that you know how to operate a boat before letting you take it out of the harbor. In the US, there are many places all over the country where you can earn your ASA (American Sailing Association) certification. The ASA dictates the national certification standards for sailing education in the US, and most charter companies accept their certification. After going through the course, there is both a written and a practical exam.

It’s a good idea to make sure that everyone who will be joining you on the vacation is willing and prepared to help out on board. If your guests are first time sailors, you might suggest that they go out on a day sail in their hometown before making the commitment to living on a boat for a week (or more). It’s not for everyone, and someone might realize they would much prefer a motor yacht or a catamaran over a sail boat (it that’s what you had in mind for your charter), or they may decide that vacationing on a boat is not for them at all. You would all be much better off knowing this beforehand.

Of all the charter options available – bareboat, skippered, and fully crewed – bareboat is by far the most affordable option. In the Mediterranean, for example, you can rent a yacht with room for 4 for less than $2,000/week, which divided by four, comes out to $500/person. That’s a great deal; try finding a hotel in that area for $500/week. And I bet the scenery from you boat beats any hotel in that price range!

In some countries, Greece being one of them, the charter companies require that you have two certified skippers on board each boat you rent. And even if the company you are chartering from is fine with just one, it does make sense to have at least one more person in your group who knows how to operate a boat. What if something were to happen to the one qualified sailor on board, even if it’s just something small, like a migraine or food poisoning? You don’t want to be stuck trying to figure out how to get the yacht back to port while the waves are getting bigger and the winds are picking up. For the sake of safety, always have at least two sailors in your group.