With so many options available, how do you choose?

The least expensive option is a bareboat charter (sailing or motor). That means no crew, you operate the boat yourself. This of course requires some skills, and you will have to provide proof to the charter company that you know how to pilot a boat. Most will ask for your Bareboat Certification or a sailing certificate. If this is not something that’s issued where you live, you can ask if a reference (verifying your sailing abilities) from your yacht club will do.

In some countries (Greece for example), you are required to have two qualified sailors on board (which makes sense; what if something happens to your appointed captain?). There are schools all over the country where you can learn the basics of sailing and get an ASA (American Sailing Association) Bareboat Certificate. If you feel you need a bit more guidance before going out on your own, consider a skipper for a few days (see skippered charter below).
Pros: You’re in charge, less expensive
Cons: You’re in charge; you have to prepare your own meals as well as everything else

A skippered charter will provide you with the boat and a captain who essentially is in charge and will operate the boat for you. You and your guests will be the crew. This option is perfect if nobody in your party wants to have the responsibility for the boat and the navigation, but still wants a hands-on experience. Some companies offer you the option of a skipper for a few days in the beginning of your trip so you can brush up on your sailing skills and get to know your chartered boat before assuming full responsibility for it.
Pros: You don’t need to know anything about boating, an affordable option
Cons: You’re not in charge

If you just want to kick back and relax and enjoy spending time on the ocean without any responsibilities, a crewed charter is ideal. It is more expensive than the options above, but you get the boat, captain, full crew and a cook. The crewed boats tend to be larger (and therefore more expensive), since they have to accommodate not only you and your guests, but the crew as well.
Pros: You don’t have to lift a finger, everything is taken care of but you decide where to go and what to do
Cons: More expensive, you’re never alone

If you have a large group with varying sailing skills, flotilla sailing is a fun option. You charter several boats (usually 6-12) and the lead boat will have a skipper, mechanic and hostess who takes care of the itinerary and will help you out when needed. The other boats in the flotilla will each be skippered by one of your group, so you do need a few skilled people.
Pros: The skipper is there in case you need help or advise
Cons: Less freedom