Some of Sicily’s most spectacular ancient ruins and atmospheric towns are set along the Ionian coast south of Messina, where most ferries and flights arrive on the island. Begin your week in Taormina, perched high above the coast and famous for its magnificent 2nd-century Greek theater, still used as a venue. Explore the highlights on a walking or Segway tour, or experience Taormina through its cuisine on a food-and-wine tour. Afterwards, take in the view from the village of Castelmola above town or the coastal outcrop of Isola Bella at the water’s edge below. No visit to the area is complete without a trip to the sputtering top of Mt. Etna, Europe’s largest active volcano. Hop on an ATV or join a guided walking tour of its towering peak, stopping to tour one of the many wine cellars scattered on the volcanic slopes.

The following day, continue south to Syracuse for a guided tour of the island of Ortygia (Ortigia), where the city was founded by the Corinthians three millennia ago. Admire the Duomo, Fountain of Arethusa, Temple of Apollo, and other highlights with a walking tour, or combine sightseeing with tastings on a food-and-wine tour. Finally, tour the ancient ruins of Neapolis Archaeological Park (Parco Archeologico della Neapolis), a UNESCO World Heritage Site.

Explore the southeastern corner of Sicily today. Join a tour of the most important towns in the Noto Valley, starting with a guided walking tour of the historic center of Noto, a treasure trove of lavish churches and palaces lining Corso Vittorio Emanuele. After stopping in Modica to take in its baroque masterpieces and sample its famous local chocolate, end with a ramble through the atmospheric jumble of crumbling palaces that make up Ragusa’s old town. 

The next day, take in the ancient Greek temples of Agrigento, dating from when Sicily was part of the vast Magna Grecia empire. Join a Valley of the Temples tour to admire these gloriously preserved ruins that date as far back as the fifth century BC. Afterwards, head inland to the Villa Romana del Casale in Piazza Armerina, an ancient hunting lodge and thermal baths that house the world’s largest collection of Roman mosaics. 

Head to the far western reaches of Sicily today to explore Marsala, in the province of Trapani. Spend the morning exploring this historic port town’s center with a walking or bike tour to take in the unique Catalan–Gothic and baroque architecture before heading out of town to the Trapani and Paceco Salt Pans Natural Reserve. Learn about this area’s long tradition of sea-salt harvesting, and admire the flamingos, cranes, and other waterfowl that now populate the reserve. In the afternoon, join a wine tour to learn about Marsala’s history of winemaking, then try to make it to the hilltop town of Erice by sunset to take in one of the most memorable views in Sicily. Stroll the charming historic center and visit the medieval castle before stopping for a traditional Sicilian dinner.

End with two days in Palermo, where Arab influence can be seen in the architecture, culture, and cuisine. Begin with a walking, bike, or Segway tour of the city’s vibrant old town, a mix of Norman, Moorish, and baroque architecture, to appreciate the 12th-century Arab-Norman churches and their exquisite Byzantine mosaics. The city is also known for its souklike street markets and local flavors that testify to centuries of Arab influence. Take a deep dive into Palermo’s distinct cuisine with a food-and-market tour or cooking class. Finally, visit the towns of Monreale or Cefalù just outside Palermo to tour their dazzling Norman cathedrals, among the most important cultural treasures in Sicily and part of a UNESCO World Heritage Site.