Sylvester the Great (Bob Hope) is a 17th-century entertainer with an act so atrocious he's exiled from England. Aboard a ship bound for America, he finds himself falling for the beautiful Princess Margaret (Virginia Mayo), a woman uninterested in love – not to mention his lousy one-liners. But when an evil band of pirates attacks the ship and captures the princess, her only hope is the cowardly comedian. Can Sylvester stop cracking jokes and muster the courage to rescue his royal love? In other words, will he and Margaret end up walking down the aisle... or walking the plank?