Pirate Dream is a pirate-themed board in Mario Party 5. It takes place on a cliffside cove with a pirate ship docked at its shore.
The board has a normal split path, a Whomp and Thwomp. The split path is towards the bottom of the map with one path going through the Pirate Ship and a shorter path though with a chance of falling to the lower path. The Thwomp acts an elevator which results in bypassing the left half of the board, ending up on the Whomp path a short bit before the start. The Whomp divides the left half of the board into two distinct paths that meet up before the start. The left default path is the safer path but, has less. The Whomp path has the capsule machine but, has more risks to be knocked off the path.
The Happening Spaces on the mine track causes a boulder to roll out of the mine, causing players off the track. The Happening Spaces along the waterfall cause the platform give way, causing the player to land on a space in front of the pirate ship. The Happening Space on the Pirate Ship causing the player to fire him/herself with the cannon to go to one of the spaces next to one of the cannon signs. The happening space at the top of the board is a Monty Mole. He gives the player a chance to dig for coins by tapping A.