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A Nantucket Sleighride is a old whaling term for when one of the small whaling boats (away from the ship) would harpoon a whale, and as the whale sounded, it would tow the boat behind it at some speed, occasionally capsizing the boat. The seas off Nantucket were rich whaling grounds, where many ships would gather, hence the term Nantucket Sleighride.

The song is simply about a young man leaving his girlfriend behind a he sailed on a (fruitless) 3 year whaling voyage.

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