When heroic, charming and handsome Sir Galavant loses his true love, the beautiful Madalena, to evil King Richard's wealth and power, he falls into a deep and drunken despair. Just as our hero hits rock bottom, Princess Isabella shows up with a quest to save her kingdom, defeat the despicable King Richard, and provide an opportunity for Galavant to reclaim Madalena. Galavant is off to become a hero again and strike a blow for true love…but first, Galavant has to fit into his old hero pants.

Galavant enters a jousting tournament against a boastful rival, Sir Jean Hamm, to test his return to heroic form (and win some much-needed traveling money and a really nice rooster). But it quickly becomes clear that Galavant is a long shot to win. Meanwhile, King Richard asks Gareth to help him become a bit more macho so that Madalena won't despise him quite so much.

A visit to Sid's hometown reveals he has not been truthful about his career path. While Galavant and Isabella back up Sid's stories, King Richard decides to throw a ball to cheer up the people of Valencia.

An encounter with land-bound pirates forces Galavant, Isabella and Sid to learn how to get over their petty squabbles and work together. Meanwhile, King Richard tries a new tact to win Madalena's love.

As our heroic trio finally approaches Valencia, they find shelter and doo-wop among local monks who have taken a vow of singing, led by Confessional Monk. Madalena, frustrated with King Richard, decides to take matters into her own hands with her own devious plot involving the besotted Chef and her winsome handmaiden, Gwynne.