You successfully blocked every enemy attack in a single (non-tutorial) battle.

You flung a turd of your own creation at an enemy.

"The Big Party" completed (New Adventures)

Patrols fought 500 battles

Possess 250,000 barrels of goods in a single game

"The bet with Pablo" completed (New Adventures)

Maximize all abilities of a captain

1,000 vessels sunk

Use up 4,000 handheld weapons in boarding combats

Win a battle against at least 60 guns with a pinnace

Reduce a nation's number of towns down to two

Possess 5,000 cannons in a single game

Get 10 linier built in the shipyard (Harbour Master)