Sicily: Crossroads of Mediterranean Civilization

Fly from the U.S. to Palermo, Sicily.

Arrive in Sicily’s capital, Palermo, whose tattered, pink majesty and rambunctious people make it one of the Mediterranean’s most enchanting cities. Transfer to the port to board Callisto and freshen up before dining at a private palazzo.

In the morning, drive to Monreale to visit its Norman cathedral, lined with a magnificent series of mosaics. Seek out the Cappella Palatina, the royal chapel built by Roger II between 1132 and 1143, a wonder of Byzantine-Arab-Norman artistry, with dazzling mosaics, an exquisitely carved wooden ceiling and magnificent inlaid marble floors and walls. Afterwards, enjoy time at leisure wandering Palermo’s charming cobblestoned streets. Sail for Riposto late in the evening.

Unwind in the morning as Callisto navigates the Strait of Messina, the mythical narrow waterway of Scylla and Charybdis. Upon docking in the quaint port of Riposto, set out on an afternoon excursion to nearby Taormina. Clinging to the edge of Mount Tauro, Taormina looks out to sea and the dramatic cone of Mount Etna. A Greek colony was founded here in 403 B.C. and prospered throughout the Hellenistic and Roman periods. Visit the magnificent Greek theater before spending time exploring on your own. Dine aboard the ship as we sail along the coast toward Syracuse.

Colonized by the Greeks in the 8th century B.C., Syracuse became one of the most powerful and prestigious cities of the ancient world, rousing the hostility of Athens. Discover the spectacular 15,000-seat Greek theater, among the most impressive to survive from antiquity, and the elliptical Roman Amphitheater, one of the largest of its kind. After a visit to the Archaeological Museum, walk the winding lanes of Syracuse’s old town, situated on the island of Ortygia, and explore the remains of the Temple of Apollo, the Fountain of Aretusa and the Cathedral, which incorporates the remains of the famed Temple of Athena. An afternoon excursion into Sicily’s southeast region, known for its Baroque town, brings us to exquisitely preserved Noto, a jewel on a plateau surrounded by olive and almond groves.

Drive to Selinunte, the most westerly Greek colony in Sicily. A highland overlooking the sea provides a tranquil setting for the expansive ruins of what was once among the island’s most progressive cities. Spend the afternoon at leisure exploring Sciacca, a picturesque seaside town built on rocky heights. Renowned for its spa during Greek and Roman times, the town is still recognized today for its stunning white sand beaches and open-air thermal baths. In the afternoon, sail to Trapani, docking at its port late in the evening.

Drive up winding roads to the medieval town of Erice, magnificently situated on a high plateau overlooking the coast. The town was known for its temple to the fertility goddess, Astarte. Peek around the magnificent 12th-century Venus Castle that was built upon the ruins of the ancient temple. Fringed by a lush park, the views from this hilltop castle are breathtaking. Continue to Segesta for a glimpse of its magnificent Doric temple, built in 420 B.C. and among the best-preserved ancient Greek sites to be found anywhere. The ruins stand in majestic solitude atop a bucolic hill with virtually no modern-day structures marring the vista, making it easy to imagine what Sicily was like in ancient times. Reboard Callisto and sail to Palermo, arriving late in the evening.

Disembark in Palermo and transfer to the airport for return flights to the U.S.