We begin at the Baroque heart of the old city, where Quattro Canti divides Palermo into four quarters, each corner presided over by a season and a Spanish monarch. Steps away, Piazza Praetoria centres on the great Renaissance fountain whose nude figures so scandalized 16th-century Sicilians that they called it the Fontana della Vergogna—the Fountain of Shame. That Sicily, then deep in Counter-Reformation piety, was ruled by a Spanish viceroy who commissioned such a work tells you something about the contradictions this city has always absorbed with remarkable grace.
At the Martorana Church, those contradictions find their most beautiful expression. Built by a Greek admiral in the service of a Norman king, its interior blazes with Byzantine mosaics laid tile by tile in the 12th century—a fusion of Arab spatial geometry, Norman patronage, and Orthodox iconography that exists nowhere else on earth.
From there we plunge into Il Capo market, one of Palermo's great sensory experiences. Fishmongers display magnificent swordfish and glistening octopus alongside the agricultural wealth of Etna's volcanic hinterland—citrus, olives, almonds—in a market culture that has changed little since the Arab traders who introduced many of these ingredients a thousand years ago.
We then make the short drive up to Monreale—the "Royal Mountain"—where Norman King William II constructed a cathedral in the late 12th century as a declaration of his kingdom's sophistication and his own piety. Its interior is among the greatest achievements of the medieval world: 6,000 square metres of gold mosaic covering walls and apse in a Biblical narrative that moves from Creation to the miracles of Christ, watched over by a monumental Pantocrator of almost unsettling authority.
Our day concludes at the Church and Monastery of Santa Caterina d'Alessandria, where Dominican nuns once perfected the art of Sicilian confectionery in its cloisters. The convent's rooftop terraces offer sweeping views across Palermo's piazzas, while the onsite bakery I Segreti del Chiostro carries those centuries-old traditions forward. As this is a large and rewarding site, we end our formal tour here so you can linger and explore at your own pace before we gather for dinner.
Overnight in Palermo.
 
Included Meal(s): Breakfast and Dinner