Redhook's Revenge is a Pirate-based board game and trivia. Choose your pirate captain and then play against two other human or computer controlled players. Then roll the dice and travel the designed number of spaces over the seaways. Your objective is to reach the home port with as much booty as possible, the player with the most wins. In addition to this however, each player has a complete inventory of items. Food and Water is required to sail properly without penalty, maps can be used to hunt for buried treasure, bales for repairs, spare canvas, a compass... a variety of items with different effects. As you travel around the seas of the Caribbean, some squares will bring about good fortune and additional supplies, other times it will be bad luck and the occasional case of scurvy.

When you land on a spot that is near a town or on the position as another player, there's the option to engage in cannon-to-cannon combat with the target. Successful combat (determined by dice rolls) will net you additional booty (as well as the spot), unsuccessful combat comes with penalties and repairs on your ship.

The game is full of trivia multiple choice questions on pirate books, movies and actors as well as facts on the geography and history of the Caribbean.