Pliny the Elder's account of Cleopatra consuming a cocktail of vinegar and a pearl in order to win a bet with Antony was considered credible in the ancient world, but many modern scholars have relegated the anecdote to the realm of fantasy. This paper identifies possible reasons for this skepticism, including the visual tradition of the story and the belief that increasing concentration always increases reaction rate. Experiments reveal that, in the case of acetic acid and pearls, the concentration found in vinegar made from wine is ideal.