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Originally Posted by SeanConnett
The charter companies may be more than willing to send you out on one of their sailboats even though your sailing experience may be minimal, but at the same time, they will also be more than willing to take your money when that inexperience causes you to tear a sail, or something else expensive. If you are comfortable with your sailing skills though, I'm certain that you'll get the keys to your very own chartered sailboat. Good luck.
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That is why there is insurance you buy when you charter a boat. Moorings makes it pretty much mandatory. There is a deductible, but it is not unconscionable (less than $1000, perhaps about $500). Everything else should be covered by insurance, unless damage was caused by gross negligence or intentionally.