Fredric (Rex Smith) was meant to be an apprentice to a pilot, but his maid mistakenly makes him an apprentice to a pirate. He is ready to leave The Pirates of Penzance.
When his maid pleads him to take her with him, he agrees, but shortly afterward, he meets the daughters of Major General Stanley (George Rose) and falls madly in love with them, so he rejects his maid Ruth (Dame Angela Lansbury).
After they say no to loving him, for he was a pirate, the fairest of them all, Mabel Stanley (Linda Ronstadt) agrees to love him. But something stirs up in the story and he and his sense of duty as a pirate are stuck in the middle.