Expedition Overview

Expedition Overview

  • Sail the shimmering waters of the Mediterranean, Tyrrhenian, and Ionian seas aboard the historic square-rigger Sea Cloud.
  • Explore the enchanting piazzas and winding alleyways of picturesque towns from Lipari to Taormina and Ortigia, in the company of local guides.
  • Visit an array of UNESCO World Heritage sites, from Greco-Roman ruins at Syracuse and Agrigento to the ancient temples of Ggantija.
  • Experience Sicily’s unique cuisine at a wine tasting in Marsala, in Erice’s renowned pasticceria, and at a private lunch in a historic castle near Taormina.



Set sail aboard the majestic four-masted Sea Cloud on a journey into the culture, history, and cuisine of Sicily and Malta. Step into the past among cities and temples left behind by the Romans, Greeks, Carthaginians, and prehistoric peoples—to name just a few. From Taormina to Gozo, wander through charming towns where modern-day life thrives amid glorious vestiges of ancient civilizations, and challenge your conceptions of Italian cuisine as you taste Sicily’s take on pizza, pastries, and wine. Savor the Sea Cloud’s elegant comfort during afternoons under billowing sails, and enjoy an incomparable Mediterranean adventure that harkens back to the golden age of ship travel.

This trip is offered in partnership with Lindblad Expeditions.


Days 1-2: U.S./NAPLES, ITALY

Depart on an overnight flight to Naples, Italy. Upon arrival, board the Sea Cloud and cast off from Naples Harbor. Gather for a welcome cocktail as we pass the lovely island of Capri and enter the Tyrrhenian Sea.

Meals Included:Day 2 (Dinner)

Sea Cloud for the entire voyage

Day 3: At Sea

Enjoy a glorious day on the sparkling waters of the Tyrrhenian Sea. Begin the morning on deck, learning about the mechanics of our four-masted vessel and observing the crew in action as they raise, rig, and trim the sails. Bask in the grace and elegance of this legendary square rigger, enjoying delicious meals, complimentary drinks, and talks by our expedition team as we sail south toward Sicily.

Meals Included:Breakfast, Lunch, Dinner

Benvenuti in Sicilia! This morning the Sea Cloud docks in Trapani, where we embark on an excursion to the mountaintop town of Erice—a mesmerizing labyrinth of alleyways surrounded by old city walls. Perched some 2,500 feet above Sicily’s western coast, the medieval town offers spectacular, panoramic views. Uncover Erice’s history with the help of local guides, and then spend some time wandering the streets on your own. Perhaps sample some of Sicily’s most renowned pastries at La Pasticceria Maria Grammatico before returning to the ship. Later, unwind on one of the ship’s sundecks or in the beautifully appointed lounge as we depart on an overnight sail along Sicily’s northern coast.

Meals Included:Breakfast, Lunch, Dinner

Our morning sail to the Aeolian Islands offers prime views of this stunning, volcanic archipelago—designated a World Heritage site. Go ashore at Lipari, where we’ll take a scenic drive around the perimeter of the island and spend time at the archaeological museum in Lipari Town, which houses an impressive collection of Neolithic artifacts. Many of the artifacts are made from local obsidian, which provided the foundation of the island’s prosperity until the arrival of the Romans in the third century B.C. Board the ship for an evening cruise to Stromboli, keeping an eye out for the island’s volcanic pyrotechnics as we approach.

Meals Included:Breakfast, Lunch, Dinner

Enjoy breakfast 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’s the mythical location of Homer’s sea monsters Scylla and Charybdis—which Odysseus had to sail past. Dock in Messina and drive up to the stunning medieval town of Taormina, which spills across the slopes at the foot of Mount Etna. Take a walk through town to an incredible third-century B.C. Greco-Roman theater, built directly into the cliff. Later, enjoy a private Sicilian lunch at the family-owned Castello degli Schiavi. Meet our hosts for a tour of this 18th-century estate and its extensive grounds, which were featured in all three of The Godfather films.

Meals Included:Breakfast, Lunch, Dinner

Sail south to Syracuse, 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. We’ll also visit a nearby limestone quarry, the Ear of Dionysus cave, and the Roman amphitheater before returning to Sea Cloud for lunch. This afternoon, venture to the enchanting island town of Ortigia to discover its charming piazzas; twisting alleyways; and impressive Duomo, built from the ruins of Sicily’s ancient Temple of Athena.

Meals Included:Breakfast, Lunch, Dinner
Day 8: At Sea

Enjoy a glorious day of sailing along the southern coast of Sicily. Join our expedition team for talks on the island’s history and culture, visit our captain on the bridge to see how the ship is navigated, or find an inviting nook where you can relax with a book and take in views of the sea.

Meals Included:Breakfast, Lunch, Dinner

Anchor in the fishing town of Mazara del Vallo and set out for the ancient Greek city of Selinunte. The site’s impressive ruins comprise the largest archaeological park in Europe. Stroll among stately temples, defensive walls, and what remains of the city’s residential and commercial quarters, and soak up the spectacular setting. After a seaside lunch, continue to Marsala where we’ll visit an excavated Punic warship at a museum devoted to the city’s Carthaginian history. Then enjoy a tasting the region’s renowned dessert wines at a historic Marsala winery, Casa Florio. Meet the ship in Mazara del Vallo tonight.

Meals Included:Breakfast, Lunch, Dinner

Our final call in Sicily is devoted to the archaeological area of Agrigento—a World Heritage site that features some of the most magnificent Greco-Roman temples of antiquity. Founded by the Greeks in the sixth 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 Valley of the Temples’ grand row of Doric temples devoted to the likes of Zeus and Heracles before returning to the ship for an afternoon on the water.

Meals Included:Breakfast, Lunch, Dinner

Malta’s strategic location in the middle of the Mediterranean has endowed the island nation with a myriad of cultural influences and a fascinating history. This morning, we visit Gozo Island, home to the World Heritage site of Ggantija. These ancient megalithic temples are over 5,000 years old, predating both the Pyramids of Giza and Stonehenge. We’ll also visit the artfully restored medieval windmill of Ta’ Kola—one of the many structures built by the Order of the Knights of St. John, who ruled the Maltese islands for centuries. This evening, celebrate our voyage with a sunset cocktail party and dinner with the ship’s captain and crew.

Meals Included:Breakfast, Lunch, Dinner

At sunrise, the Sea Cloud enters one of the finest harbors of the Mediterranean: Valletta, Malta’s capital city, surrounded by fortifications that date back to the 16th century. Be on deck with your camera as we make our final approach beneath the city’s impressive bastions, walls, and towers. Disembark after breakfast and transfer for the airport for your flight home. Alternatively, opt to continue your exploration of Malta on a post-trip extension.

Meals Included:Breakfast