You play the pirate Captain Gingerbeard, who is on a quest to find the Treasure Island. You will navigate from island to island, disabling enemy ships with your own ship, seize them and fighting the enemy crew on an one-on-one fight, including the enemy captain. You will attack enemy forts, trying to escape mazes, and gamble with the harbour master of neutral islands for replacements of your crew.

Pirates of Treasure Island is a strategy puzzle game. A 12x15 rows large playfield is filled to a specific degree with four different symbols. You have to click on a group of at least three blocks of the same type to get them removed. If you remove more than three at once, you earn more points. But with each click, new items dropping in, filling more and more of the playfield. If you run out of possible combinations, you can redraw the playfield as many times you want, but each time will cost you points already earned. There are four different types of blocks. Besides actually getting points for the blocks you remove, you will also use them to manipulate the environment accordingly to your current situation.

To attack an enemy ship, you load your cannon by clicking a cannonball from the puzzle playfield. Your crew will then load the cannon for you. Now you have three different possible blocks you can use, one for the middle ship, one for the right ship, and one for the left ship. Your cannon will fire as soon as you click the block group of your choice. The fourth block group in this example will always miss the ships (shot in the water). While you are firing, the enemy ship(s) will firing too. On each second hit you will loose one of your ten crewmen (first shot wounds him only) and a part of your playfield will drop from the screen.

The game runs in real time. While you may still try to find a proper block group in the huge puzzle field, the enemy ships will continue firing normally, regardless of whether you fight or not. Or, in the worst case, when you are fighting the enemy captain, you must parry his attacks with a proper block group, or you will instantly loose your crewman, who is fighting for you.