In Picaresque, you will choose one player to be the Game Master (GM); everyone else is a player. The GM will describe the scenes the players journey through and introduce the trials they face. The players will devise plans to overcome the trials in order to get to their Journey's End.

The game takes place over a series of stages, each representing a stage of the journey. Each stage has four parts which take place in turn:

1. Create a new scene: The GM places a new scene between the current scene and Journey's End. This is the next place characters are trying to get to on their journey, which will eventually lead to the Journey's End.

2. Explore the scene: Players roleplay freely, exploring the current scene and looking for ways to get to the new scene.

3. Introduce the Trial: The GM selects a Trial card as an obstacle in their way. The players devise a plan to overcome the Trial.

4. Face the Trial: At a climatic moment in the plan, the GM pauses the roleplay to resolve the Trial.To succeed, the players require a total greater than or equal to 7; otherwise the players fail. Reveal the top 2 cards of the deck and add their Values, then applying bonuses.

If players passed the trial, they earn a Boon. After overcoming two trials, the next scene is Journey's End. Players must overcome one last Trial to reach their final destination and succeed in their quest.