In Geoffrey Chaucer's The Canterbury Tales, the Squire is likely the youngest pilgrim at about twenty years old, and he never sleeps too much (because he is too busy courting the ladies to worry about sleep).

We read about the Squire in the General Prologue. The Squire is the Knight's son, but he is not much like his father at all. Rather, he is “A lovyere and a lusty bacheler” with curly hair (he seems to give the curls a little help). This is an agile, strong young man who can carry himself well in a battle but is far more interested in impressing the ladies than in winning virtues. He dresses well and sings much, even composing his own songs. He dances and jousts, writes and draws, and he is for all purposes an impressive young man.

His sleeping habits, however, leave something to be desired. He loves quite passionately in the night, we are told. Yet he is still courteous and humble, willing to serve his father as he strives to become a knight himself.