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Set sail aboard the majestic four-masted Sea Cloud on a journey into the culture, history, and cuisine of Malta and Sicily. Step into the ancient past among cities and temples left behind by the Greeks, Carthaginians, and prehistoric peoples—to name just a few. In Taormina and Valetta, wander through charming towns where modern-day life thrives amid glorious vestiges of Greco-Roman civilization, and challenge your conceptions of Italian cuisine as you taste Sicily’s take on pizza, pastries, and wine. Then soak up the elegant comfort of our ship during four relaxing days at sail on the Ionian and Aegean seas on our way to Athens.
Sail the shimmering waters of the Mediterranean, Tyrrhenian, Ionian, and Aegean seas aboard the historic square-rigger Sea Cloud
Explore enchanting piazzas and winding alleyways of picturesque towns from Cefalù to Lipari and Ortigia in the company of local guides.
Visit five UNESCO World Heritage sites, from the storied city of Valletta to ancient Greco-Roman ruins at Agrigento and Syracuse.
Experience Sicily’s unique cuisine at a wine tasting in Marsala, in Erice’s renowned pasticceria, and at a private dinner in a historic castle near Taormina.
Itinerary - 15 Days
Days 1 & 2 — U.S./Valletta, Malta
Depart on an overnight flight to Valletta, Malta’s capital city, whose strategic location in the middle of the Mediterranean has endowed it with a myriad of cultural influences and a fascinating history. Get an introduction to the island during a riveting audio-visual show tracing 7,000 years of Maltese history and a visit to Fort St. Elmo, the seaside stronghold presiding over the Old Town. Then settle into your cabin aboard the exquisite Sea Cloud, and if you wish, head back into town this evening. (D)
Day 3 — Gozo
Rise early to catch mariners climbing lines and setting the magnificent sails of the Sea Cloud by hand. Today we visit Malta’s 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. This evening, gather for a welcome cocktail and dinner with the ship’s Captain and crew. (B,L,D)
Day 4 — At Sea
Enjoy a full day on the sparkling waters of the Mediterranean. Attend a talk and demonstration on the mechanics of our four-masted vessel, or find an inviting nook where you can relax with a book and take in views of the sea. Tonight we’ll get our first taste of Sicily at a wine tasting that features reds and whites from the nearby island. (B,L,D)
Day 5 — Agrigento, Sicily
Benvenuti in Sicilia! Our journey begins at Agrigento’s Valley of the Temples. Founded by the Greeks in the seventh 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 Herakles before returning to the ship for an afternoon on the water. (B,L,D)
Day 6 — Selinus and Marsala
Anchor in the fishing town of Mazara del Vallo and set out for the ancient city of Selinus. The site’s impressive ruins comprise one of the largest archaeological parks in the world. Stroll among stately temples, town walls, and what remains of the city’s residential and commercial quarters. Continue to Marsala where we’ll visit an excavated Punic warship and a museum devoted to the city’s Carthaginian history before tasting the region’s renowned dessert wines at a local vineyard. (B,L,D)
Day 7 — Erice
After docking in Trapani, we’ll ascend to the medieval mountaintop town of Erice, a mesmerizing labyrinth of alleyways surrounded by old city walls. Uncover its fascinating history with the help of local guides, and then spend some time wandering the streets on your own. Sample some of Sicily’s best cakes at Maria Grammatico’s renowned pasticceria before returning to the ship. Tonight, we’ll hear a talk on the history of the ship and enjoy an opportunity to see some of its original staterooms. (B,L,D)
Day 8 — Cefalù
Take part in an on-deck photography workshop before the ship drops anchor near Cefalù. Regarded as one of Sicily’s most beautiful towns, this seaside gem is framed by the sweeping headland rock of La Rocca. We’ll tour Cefalù on foot, including the 12th-century Norman cathedral that dominates the cityscape. We dock here overnight, providing extra time to tackle La Rocca or explore the town on your own this evening. (B,L,D)
Day 9 — Lipari/Stromboli
Our morning sail to Lipari offers prime views of the Aeolian Islands, a World Heritage site. We’ll take a scenic drive around the perimeter of the island and spend time in Lipari Town, browsing the impressive collection of Neolithic artifacts at the archaeological museum. Board the ship for an evening cruise to Stromboli, keeping an eye out for the island’s volcanic pyrotechnics as we approach. (B,L,D)
Day 10 — Strait of Messina/Taormina
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. This afternoon, we drop anchor off the coast of Taormina, a picturesque medieval town that 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. Tonight, we’re invited to a private dinner at a family-owned castle. Meet our hosts for a tour of the 18th-century estate, which was featured in several Godfather films. (B,L,D)
Day 11 — Syracuse
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 still in use today. After lunch, visit 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. (B,L,D)
Days 12 through 15 — At Sea/Methoni Castle, Greece
Enjoy a leisurely crossing of the Ionian Sea en route to Greece, following the winds and taking advantage of spontaneous opportunities to swim or explore along the way. Stop for a visit to Methoni Castle outside of Pylos, and spend a final day sailing the Aegean Sea. (B,L,D)
Day 16 — Piraeus/Athens/U.S.
Disembark in Piraeus this morning and transfer to the airport in Athens to catch your flight home. (B,L,D)
Travelers should be in good health and comfortable walking or standing for extended periods of time. Daily activities may include city walking tours, visits to sites, game drives, or easy hikes, with options for more physical activities such as hiking, kayaking, snorkeling and biking.
Click here for a description of all activity levels.