Spring (April and May) is the best time to visit Pitigliano. The tuff hillsides are green, the light is clear, the crowds have not arrived, and the vie cave are at their most atmospheric with the damp of winter still in the rock. Summer (June to August) is hot and increasingly busy, particularly in July and August when northern Italian and German tourists fill the town.
September and early October are excellent — the vintage is underway, the heat eases, and the olive groves around the town are preparing for harvest. Winter is quiet to the point of feeling empty; many restaurants and shops reduce their hours or close. The surrounding Maremma landscape in winter, when the wild boar are hunted and the forests are bare, has a bleakness that suits its character.
The Festival of Lights (Torciata di San Giuseppe) takes place on 19 March: a torch-lit procession through the dark lanes of the old town, a tradition that predates the current saint's-day framing and has the atmosphere of something much older.