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The last time I chartered was a long time ago, but I talked with the Moorings person at the Chicago Strictly Sail show, who said the procedure is the same. Their charter agreement specifies that they have the right to have you checked out by an experienced skipper. If you pass, you can sail the boat yourself. If not, then you're obliged to hire one of their skippers to accompany you. The Moorings said they don't charge for the checkout sail, but if you aren't approved, they'll charge, of course, for the hired skipper who will acccompany you. I always "tipped" my checkout skippers. They aren't hard to satisfy, but they aren't going to let fools or incompetents take out their expensive boats alone. "Back in the day" when I was chartering, I thought of the checkout sail as an opportunity to learn something new. For example, I asked one checkout skipper to show me how to back a sailboat into a slip, and he was glad to do so. Whenever I chartered a boat, I always thought of some boat handling skill that I wanted to learn, to make the most of the opportunity.
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