Bareboat charter is for the more experienced person who has been sailing before. In fact the boat owner will insist on some type of qualification from a national authority before agreeing on the charter. This qualification will be something like an Offshore Skipper Certificate, depending where you are from. On a bareboat charter you are your own skipper, mate, mechanic, deckhand, chef and dinghy driver. Whilst on charter it is up to you to arrange all the watch keeping, safety, daily routine etc. To be able to take on a bareboat charter you will be familiar with a yacht routine and know what to do. If you are a little rusty or not familiar with the type of yacht then you may wish to employ a skipper for the whole charter or for just a few days. You will quickly learn from the skipper before taking over on your own but you must realize that the skipper will require a cabin for his time on board so allow for that when planning your vacation.
Yachts offered for bareboat charter are more than likely to be older yachts that have been used as instructional yachts as well as hired by less than accomplished sailors. They are unlikely to be in pristine condition as they have been used and have acquired bumps and scratches from contact with jetties and inside galley spills leaving their mark. However you will still have lots of fun with good value for money a the charter rate will be lower for this type of yacht.
The size of the yacht could be anything up to 60 feet and will be comfortable and easy to handle for you and your party. Single hull sailing yachts, catamarans and power yachts are all available for the same cost or less than the cost per person on a mid range cruise ship. If you wish to employ a skipper or a chef/deckhand then obviously the cost will increase to pay their wages, possibly up to $300 per day for the skipper, who will do most of the work on board and make life easier for you.
If you are lacking the experience or would feel happy with company nearby then you might choose to take a flotilla charter instead. This allows you to sail your own yacht but have the support of a professional skipper and crew member leading the flotilla on their own yacht. You sail in company with other yachts and the agenda is arranged by the flotilla skipper who has all the local knowledge to make your vacation pleasurable. As you acquire knowledge and become more confident you may wish to sail independently of the flotilla but arrange to meet up with them at the next harbor or anchorage. You will still be able to stay in contact with the flotilla by radio in case you need help.
The other category is that of a crewed yacht. This can be any amount of crew from just a skipper/owner through to a large yacht with captain, mate and full crew. A husband and wife crew on their own yacht is quite common where the wife will do all the cooking and domestic chores and lend a hand crewing as well. You will not be asked to do too much work but of course you can be involved as much as you want. So what is the difference here to the skippered bareboat, it is the fact that the yacht is owned by the husband and wife team and will be in better condition and well maintained. They will take greater pride in their yacht and will see themselves as hosts rather than paid crew.