Adapted from the novel by Rafael Sabatini, this swashbuckling classic chronicles the adventures of Peter Blood (Errol Flynn), 17th Century physician turned pirate. Sold into slavery in Jamaica he makes an enemy of the brutal Colonel Bishop (Lionel Atwill) and then falls in love with with the Colonel's niece, Arabella Bishop (Olivia de Havilland), before he masterminds a daring escape with his fellow prisoners and becomes a gentleman/rogue pirate of the Caribbean with the sinister help of Levasseur (Basil Rathbone).

When Richard the Lionheart, the King of England, is taken captive by Leopold of Austria while returning from the Crusades, his brother Prince John (Claude Rains) takes power and proceeds to oppress the Saxon commoners. Prince John raises their taxes, supposedly to raise Richard's ransom, but in reality to secure his own position on the throne. One man stands in his way, Robin, the Earl of Locksley (Errol Flynn), otherwise known as Robin Hood. He is outlawed for stopping Sir Guy of Gisbourne (Basil Rathbone) from arresting Much (Herbert Mundin) for poaching one of the king's deer. Robin goes alone to see Prince John at Gosbourne's castle and announces to John's assembled supporters and a contemptuous Maid Marian (Olivia de Havilland) that he will do all in his power to oppose John and restore Richard to his rightful place. He then escapes, in spite of the efforts of John's men.

His lands and title now forfeit, Robin takes refuge in Sherwood Forest with his friend Will Scarlet (Patric Knowles). There they meet and recruit Little John (Alan Hale, Sr.), Friar Tuck (Eugene Pallette), Much, and a band of outlaws. Soon, Prince John and his Norman cronies find themselves harassed beyond all bearing. But then Prince John devises a cunning plan to capture Robin Hood - will it work?