Once the royal marriage logistics are underway, Buttercup is brought into the Great Square to meet her subjects as Prince Humperdinck's bride-to-be. She walks among the people and they all adore her—or so we are led to believe until she is kidnapped by three of her subjects while she is in the forest, riding her horse. The three men, Vizzini, Fezzik, and Inigo Montoya, take her onto a ship and discuss their mission to kill her to start a war between Guilder and Florin. She is quite frightened, as one might imagine, so she leaps into the sea. Sharks surround her and when the moon lights up the dark sky, Fezzik pulls her back onto the boat. At this point, the narrator interrupts to reassure us that she does not die here: "Well, since the book's called The Princess Bride and since we're barely into it, obviously, the author's not about to make shark kibble of his leading lady."

Around this time, Inigo notices a ship following them toward the Cliffs of Insanity, and Vizzini dismisses it as inconceivable. Yet the black ship behind them gains, and our three bandits and their stolen princess scale the cliffs on a rope draped around Fezzik's enormous body, and they arrive at the top to see that a man in black is following them up. At the top, Vizzini unties the rope, and to everyone's astonishment, the man does not fall, but rather climbs with his hands. This merits another "Inconceivable!" from Vizzini, who them instructs Inigo to kill the man in black and promptly darts away with Fezzik and Buttercup in tow.

The narrative includes a flashback history into Inigo's childhood. We learn that he and his father, Domingo Montoya, lived high in the hills of Spain, where his father grudgingly and surreptitiously made back-order swords for Yeste, the most famous Madrid sword-maker. One day a six-fingered count, Count Rugen, approached and requested a special sword, and Domingo spent a year slaving over this, his magnum opus, only to have the Count return, refuse to pay its full price, and promptly kill Domingo. Inigo, a boy at the time, left his village and learned everything he can about sword fighting to seek his revenge, and soon was declared by Yeste to be a wizard, the highest rank in steel. But unable to find the six-fingered count, Inigo soon lost steam and became a drunkard, the state in which he was found and employed by Vizzini.

We return to real time, where an impatient Inigo helps the man in black up to the top of the cliffs. They duel, accompanied by a fantastic description of technique and terrain. Both begin with their left hands and switch to their right once they tire, demonstrating even further their high and matched abilities. Finally the man in black wins, but instead of killing Inigo he simply knocks him out with the butt of his sword, and then runs off in pursuit of the princess. Vizzini espies the man in black running toward them and is astonished, so he leaves Fezzik to dispose of him at last.

Here we have a flashback history into Fezzik's childhood, and we learn that his parents encouraged him to use his strength and size (he was an extremely large Turkish baby) to discourage his classmates from bullying him. Fezzik, a tearful and worrying child, did not want to fight but obeyed his parents anyway, and soon he had defeated all of the strongest men in Turkey. He moves through Greece, Korea, and time after time the audience booed Fezzik because the ease with which he fought made the competition seem unfair. Soon he began fighting gangs, since individuals were too easy. After Fezzik's parents died, he was left alone and lonely in Greenland where he comforted himself with rhymes until Vizzini found him. As unpleasant as he is, Vizzini did serve as the ministering angel for both Fezzik and Inigo.

Back near the Cliffs of Insanity, Fezzik challenges the man in black to a wrestling match, and unbelievably the man in black wins by clinging to Fezzik's neck and blocking his windpipe. The man in black leaves Fezzik alive, but barely, and he runs off to seek Vizzini, who is waiting at a picnic area with Buttercup. Thus ensues the famous Battle of Wits, where the man in black places iocane powder in wine and waits for Vizzini to choose which glass is left unpoisoned. Through a winding jigsaw process of reasoning, Vizzini examines the situation from many angles, switches the goblets while the man in black was distracted, and drinks from his own goblet. He dies laughing at how cleverly he fooled the man in black.