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.

Bad advice results in Galavant and the crew being shipwrecked, and they end up traveling by foot in order to get back to Richard’s kingdom. Later, Galavant and King Richard find themselves at The Enchanted Forest Pub in West Hollow-wood where they are forced into working there by the owner who sees Galavant in a different light.

Meanwhile in Valencia, Madalena rules as Queen, and Gareth demands his due when he is announced as King, with Sid as his assistant. Elsewhere in Hortensia, Isabella is imprisoned in her jewel box by her 12-year-old cousin as her parents prepare for their wedding.