Sailing the Ancient Shores of Sicily and Malta aboard Sea Cloud

Days 1-2

Naples, Italy / Embark Ship

Arrive in Naples on an overnight flight. Board the legendary Sea Cloud and cast off from Naples’ harbor. We gather for a welcome cocktail as we pass the island of Capri’s rugged coast and enter the Tyrrhenian Sea. Meals are on your own except for dinner on Day 2.

Day 3

At Sea

Join our 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 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 as we sail south toward Sicily.

Meals Included: Breakfast, Lunch, Dinner

Day 4

Erice, Sicily / Marsala

After Sea Cloud docks in Trapani this morning, we depart on an excursion to nearby Mount Erice to visit the medieval town of Erice. Perched 750 meters 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 we continue 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. We finish with a visit and tasting at a winery before returning to Sea Cloud in Trapani. Sail overnight to Porto Empedocle for Agrigento.

Meals Included: Breakfast, Lunch, Dinner

Day 5

Agrigento / At Sea

We dock in Porto Empedocle this morning for our 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 and cast off for a relaxing afternoon under sail.

Meals Included: Breakfast, Lunch, Dinner

Day 6

Valletta, Malta

At sunrise, we enter one of the finest harbors of the Mediterranean: Valletta, Malta’s capital city, surrounded by daunting limestone fortifications that date back to the 16th century. Be on deck with your camera as we make our final approach beneath the city’s bastions, walls, and towers. Malta’s glorious waterfront settings, its views, the historic cities and towns, and amazing buildings combine to make a visit here a wonderful experience.

We spend the morning touring the city, a UNESCO World Heritage site. Drive to the Upper Barracca Gardens, located on the highest point of the 16th-century walls that the Knights of Saint John built to protect their city. Take in the remarkable views of the Grand Harbor, Fort Ricasoli, and the Three Cities—Birgu, Senglea, and Bormla. Continuing through Valletta’s historic streets, we tour St John’s Co-Cathedral, complete with elaborate inlaid marble tombstones and monumental artwork.

Then we visit Malta’s old capital, Mdina, a walled medieval city dating from the Norman and baroque periods, that has been inhabited for thousands of years. Walk through the city’s streets and enjoy the fantastic view from the bastions. Marvel at the impressive Mdina Cathedral and then take a short drive to the Rotunda of Mosta, the fourth-largest unsupported dome in the world. During World War II, a bomb pierced the dome and landed, unexploded, in the church. Return to Sea Cloud docked in Valletta, where our guests may wander on their own after dinner.

Meals Included: Breakfast, Lunch, Dinner

Day 7

Gozo / At Sea

This morning we visit Malta’s “second island,” Gozo, with our 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. We also 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 and an afternoon cruising back to Sicily, with hopes of sailing in the afternoon winds.

Meals Included: Breakfast, Lunch, Dinner

Day 8

Siracusa, Italy

Wake this morning to Siracusa, a city that once rivaled Athens in cultural and economic wealth. We 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. We 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 Ortigia 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.

Meals Included: Breakfast, Lunch, Dinner

Day 9

Taormina / Messina

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, we 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. We then return to Sea Cloud, docked in the port of Messina. Enjoy dinner on deck as our vessel follows the wake of Odysseus through the narrow Strait of Messina, the bustling waterway that separates Sicily from the boot of Italy. It is the mythical location of Homer’s monsters Scylla and Charybdis—the rock and the hard place through which Odysseus had to sail.

Meals Included: Breakfast, Lunch, Dinner

Day 10

At Sea / Lipari / Stromboli

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. We sail in the morning with the islands of Vulcano and Stromboli in view, anchoring for the afternoon at Lipari. Here we 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. We 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, we enjoy dinner on deck as Sea Cloud cruises the 25 miles to Stromboli—and, with a little luck, we see some of the pyrotechnics of this active volcano, a perfect way to end such an adventurous voyage.

Meals Included: Breakfast, Lunch, Dinner

Day 11

At Sea

After such an action-packed voyage, we take a full day for sailing, reflection, and relaxation. Join our expedition staff for talks on the Lido Deck, as the captain takes advantage of the prevailing wind for optimal sailing. Aboard Sea Cloud there is time to catch up on journals, review photos, 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, we celebrate our voyage with the captain’s farewell cocktail party and dinner at sunset.

Meals Included: Breakfast, Lunch, Dinner

Day 12

Naples / Disembark Ship

Disembark in the port of Naples this morning and transfer to the airport for your flights home.

Meals Included: Breakfast