Sailing the Ancient Shores of Sicily and Malta Aboard Sea Cloud II

Arrive in Valletta, Malta’s capital city and a UNESCO World Heritage site, surrounded by daunting limestone fortifications that date back to the 16th century. Embark Sea Cloud II in the late afternoon, settle in and enjoy the first night onboard. Arrival Time: Arrive before 4:00 p.m. local time. Arrival City: Valletta, Malta

Join your expedition leader for a play-by-play description of the crew in the rigging and the action of the setting of square sails, staysails and jibs as Sea Cloud II shows her full glory. Bask in the comfort and intrigue of this distinctive square-rigger—enjoy delicious meals, complimentary drinks and talks by the expedition staff as you sail north toward Sicily.

Dock in Porto Empedocle this morning for the next call: Agrigento’s Valley of the Temples, a UNESCO World Heritage site that is a collection of some of antiquity’s most magnificent Greco-Roman temples. Founded by the Greeks in the 6th century B.C., the site served as a prominent city in Magna Graecia before eventually changing hands between the Carthaginians, Romans, Byzantines, Arabs and Normans. Explore the valley’s grand row of Doric temples devoted to the likes of Zeus and Heracles. Return to Sea Cloud II and cast off for a relaxing afternoon under sail.

After Sea Cloud II docks in Trapani this morning, depart on an excursion to the nearby medieval town of Erice. Perched 750 meters (about 2,461 feet) above Sicily’s western coast, the panoramic views from the walled town are spectacular. Explore Erice with local guides and take time to wander on your own. Perhaps stop in at the renowned Pasticceria Maria Grammatico, or one of the many other local favorites, before continuing to the town of Marsala. Famous for its fortified wines, this port city also houses an excellent museum devoted to its Punic (Carthaginian) history, as well as an excavated Punic warship and a recently opened excavated Roman merchant vessel. Finish with a visit and tasting at a winery before returning to Sea Cloud II in Trapani.

Grab your favorite deck chair, indulge in a delightful book and listen to the ship part the surf as you sail along Sicily’s northern coast. Weather permitting, stand on deck and watch the orchestrated frenzy of crew members go aloft in the web of Sea Cloud II’s riggings to handset her sails. Or attend a presentation by your historian or cultural expert about the region’s rich history.

Disembark Sea Cloud II in Messina and drive up to the beautiful town of Taormina, which spills across the slopes at the foot of Mount Etna, dominating to the south. This medieval town boasts the pedestrian-friendly Corso Umberto, lined with exquisite buildings, and one of the world’s most interesting cultural sites: the Greco-Roman Theater. This remarkable theater was built right into the cliffside, overlooking the vast sea below, in the third century B.C. From Taormina, continue to the Castello degli Schiavi, an 18th-century privately owned villa, for a special private lunch. Meet members of the family that still owns the villa and explore the extensive buildings and grounds that served as the setting for many scenes in The Godfather films. Return to Sea Cloud II, anchored off the town of Giardini Naxos, and enjoy happy hour and dinner as we sail to our next destination.

Wake this morning to Siracusa, a city that once rivaled Athens in cultural and economic wealth. Explore the archaeological park which showcases one of the world’s largest theaters of antiquity, a 15,000-seat arena hewn from bedrock, which is still in use today. Visit the nearby limestone quarry, the cave of “Dionysus’ Ear” and the Roman amphitheater before returning to Sea Cloud II for lunch. This afternoon, enjoy a break from the action-packed voyage by taking time to reflect and relax as you sail to Gozo. Join your expedition staff for talks, sample a collection of Sicilian wines or simply enjoy the thrill of an extended sail on this remarkable square-rigged tall ship.

This morning, visit Malta’s “second island,” Gozo, focusing on the ancient megalithic temples of Ġgantija, a UNESCO World Heritage site. Older than both the Pyramids of Giza and Stonehenge, the giant structures of Ġgantija were built by civilizations that thrived here more than 5,000 years ago. Visit the restored medieval windmill of Ta Kola—one of the many structures built by the Order of the Knights of Malta, who ruled the Maltese islands for centuries—before returning to Sea Cloud II. This evening, as you sail toward Valletta, celebrate your voyage with the captain’s farewell cocktail party and dinner at sunset.

Be on deck this morning with cameras ready as you enter one of the most attractive harbors in the Mediterranean by tall ship. Disembark and drive to the city’s highest point, the Upper Barracca Gardens, and take in the sweeping view. Tour St. John’s Co-Cathedral with its elaborate inlaid marble tombstones and monumental artwork. After lunch onboard, opt for free time in Valletta, or continue your exploration with a visit the old capital of Mdina: walk along the ancient city walls and marvel at the feat of engineering undertaken to build the Rotunda of Mosta, one of the largest unsupported domes in the world. Enjoy a final dinner aboard Sea Cloud II this evening.

Disembark in the port of Valletta this morning and transfer to the airport for your flights home. Departure Time: Anytime Departure City: Valletta, Malta