Sailing The Ancient Shores of Sicily & Malta

This morning visit Malta’s “second island,” Gozo, with a focus 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. Also visit the artfully 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 the ship and an afternoon cruising back to Sicily, with hopes of sailing in the afternoon winds.

Join the 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 the ship shows her full glory. Bask in the comfort and intrigue of this legendary and historic square-rigger—enjoy delicious meals, complimentary drinks and talks by the expedition staff while sailing south toward Sicily.

After Sea Cloud docks in Trapani this morning, depart on an excursion up nearby Mount Erice to the intriguing medieval town of Erice. Perched 2,460 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. Perhaps stop in at the renowned Pasticceria Maria Grammatico, or one of the many other local favorites, before more exploration in 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 Marsala’s most historic winery, Casa Florio, before returning to Sea Cloud in Trapani. Sail overnight to Porto Empedocle for Agrigento.

The next call is devoted to 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 the ship and cast off for a relaxing afternoon under sail.

Grab your favorite deck chair, indulge in a good book and listen to the ship part the surf while sailing along Sicily’s southern coast. Weather permitting, stand on deck and watch the orchestrated frenzy of crew members go aloft in the web of Sea Cloud’s riggings to handset 30 sails. Or, attend a presentation from the onboard historian or cultural expert about the region’s rich history.

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. Also visit the nearby limestone quarry, the cave of Dionysus’ Ear, and the Roman amphitheater before returning to Sea Cloud for lunch. This afternoon, venture to the enchanting island town of Ortygia to discover its numerous little piazzas and twisting alleys. But the main feature is the Duomo, or Cathedral, which was built from the ruins of Sicily’s ancient Temple of Athena. The history of Sicily can be told in the walls of this incredible construction.

Anchor off the port of Giardini Naxos and drive up to the intoxicatingly beautiful town of Taormina, which spills across the slopes at the foot of Mount Etna, dominating to the south. The stunning medieval town boasts the now-fashionable walk on the pedestrian Corso Umberto, lined with exquisite buildings, and ends at the Greco-Roman Theater. This unforgettable theater was built right into the cliffside, overlooking the vast sea below, in the 3rd century B.C.

From Taormina, continue to the Castello degli Schiavi, a phenomenal 18th-century privately-owned villa, for a very 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. Return to the ship, docked in the port of Messina. Enjoy dinner on deck as the vessel follows the wake of Odysseus through the narrow Strait of Messina, the bustling waterway that separates Sicily from the boot of Italy. It’s the mythical location of Homer’s monsters Scylla and Charybdis—the rock-and-the-hard-place whirlpools through which Odysseus had to sail.

The Aeolian Islands are not only famous for the winds of the god Aeolus, but also for some of the most well-known classical volcanoes. Sail in the morning with the islands of Vulcano and Stromboli in view, anchoring for the afternoon at Lipari. Here, go ashore for a scenic drive around the perimeter of the island, with fantastic views of the other Aeolian volcanoes, before returning to the main town. Visit the small but surprising archaeological museum that has an extensive collection of Neolithic artifacts made from the local obsidian, which provided the foundation of the island’s prosperity during the Greco-Roman era. This evening, enjoy dinner on deck as the ship cruises the 25 miles to Stromboli—and with a little luck, see some of the pyrotechnics of this active volcano.

After such an action-packed voyage, take a full day for sailing, reflection and relaxation. Join the expedition staff for talks on the Lido Deck, as the captain takes advantage of the prevailing wind for optimal sailing. Aboard Sea Cloud there will be time to catch up on journals, photo reviews, questions, sample a collection of Sicilian wines, and to simply enjoy the thrill of an extended sail on this historic square-rigged tall ship. This evening, celebrate your voyage with the captain’s farewell cocktail party and dinner at sunset.

Disembark after breakfast and transfer to the airport for flights home.