about a million years ago. We'd picked it up in Martinique and were heading from St. Lucia to St. Vincent with a charter party aboard. Guesty was steering (as I recall) and cook and I were hanging out aft. I hear this "thwunk" -- look up to see the rig still standing, look back at cook to say, "Did you hear that?" and over her shoulder, rapidly disappearing in the distance was an upside down gray thing.
Well, we retrieved it, tied a heftier painter to it, and carried on.
Week or two later, we're sailing north toward Bequia, lovely brisk trade, little bit of a squall, and in stead of accelerating, the boat slows down. I look back. No dinghy. I look down, and it's playing dolphin under the stern, upside down.
After that, We took it on deck for the passages.
And no, it didn't have the motor on it!!