There are many places in the world where theorizing about planning barely finds fertile ground to grow. Institutional planning, promoted by nepotistic political representatives, is rarely counteracted by bottom-up practices closer to people's needs and dreams. Moreover, the few community organizations and grassroots associations that do exist often find it difficult to increase social consensus, affect decision making, and improve people's lives. In Sicily, Italy, the problems are compounded by the centuries-long history of mafia territorial dominance. Can planning help in such contexts? Can it, in particular, help in weakening the mafia's social consensus and ability to influence every component of society (economics, politics, culture)? If so, what kind of planning is needed? And who should implement it? This paper addresses these questions, telling the story of one "difficult" place-the area of the historical market of Catania (eastern Sicily), where a participatory action-research experience was carried out by the LabPEAT, University of Catania. The paper ends with an optimistic thought: participatory action-research-an approach to action in which a reflective rationality helps practitioners and communities to overcome dilemmas along the way, and to conceive of actions that go beyond the habitual-has shown potential to inform institutional and community planning choices in a way that counteracts Mafia hegemony.