Disclaimer: I don't own PotC. Sadly.
A/N: Ooh, look! Another PotC drabble. I'm now engaged in the forum 'A Broken Compass' which provides one-word prompts for drabbles, so more will be in coming. This one is a little rushed and not utterly fantastic---the prompt was Hotel Caribbean, as in the song, but having never heard it, I just went with my first thoughts.
Oh yes, I believe we all know the lady in question.
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Jack's head thumped softly into the sand, filling his dreadlocks with the tiny grains. As he proudly (most of the times) bore the title, excuse, and reason of 'pirate', he had slept the night in many different places. More than a few dozen wenches' arms, on the warm beach of a pillaged town, on his Pearl, slumped in corners of taverns, or piles of hay—really, anywhere. And a few delicious times had been spent in some noble's bed, with soft pillows and mattresses that he had pillaged secretly for his own cabin, even if the feathers and ticking would quickly rot.
But despite all of the places Jack Sparrow had slept over the course of his life, perhaps this one was the best yet. On a beach, drinking himself into a stupor, with the loveliest pair of ankles he had yet to see on a woman measuring out the steps away from him. Oh yes--the woman was holding a bottle of rum from which she was taking numerous sips. As far as Jack Sparrow was concerned, right now he was in the finest hotel in the Caribbean.