Most the boats for rent by the Moorings are privately owned and just operated by the Moorings, which is US based. The do have insurance built into the rental cost. I think they don't mind if their boats get trashed by amateur sailors, which happens a good amount, because they need to turn over their boats every few years anyway. What better way to buy a new boat than with insurance money from an old boat.
You hear it all the time over the radio, distress calls from people who found themselves in bad situations. The Moorings have rescue boats around the islands to respond to these calls because of their frequency.
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