A balance of sailing, savoring & exploring idyllic isles

Expeditions aboard Sea Cloud are crafted to offer you a panoramic experience of the archipelago. Within hours of arriving in the Mediterranean, you’ll experience an abundance of history and culture. Each day will deliver opportunities to relish sailing on a true square-rigger and exploration of idyllic islands and ancient sites. Flexibility is a hallmark of our expedition style so we’ll take advantage of wind and weather to ensure you get the most out of each moment of your voyage. Select 2021 or 2022 below to be sure you view the correct itinerary for each year.

Important Note: 2022 departures follow a slightly modified itinerary:

Printable Itinerary Summary (2022 Departures)

  • DAY 1-2: U.S./Naples, Italy/Embark

    Fly overnight and arrive in Naples. Board the legendary Sea Cloud and cast off from Naples’ harbor. We’ll gather for a welcome cocktail as we pass the island of Capri’s rugged coast and enter the Tyrrhenian Sea. (Day 2: D)

  • DAY 3: At Sea

    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, stay sails, 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. (B,L,D)

  • DAY 4: Erice/At Sea

    After Sea Cloud docks in Trapani this morning, we depart on an excursion up nearby Mount Erice to the intriguing 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 as well. Perhaps stop in at the renowned Pasticceria Maria Grammatico, or one of the many other local favorites, before returning to the ship. Back aboard Sea Cloud, the deck crew heads aloft to set sails for the afternoon, with hopes for steady winds and an overnight sail along Sicily’s north coast in the Tyrrhenian Sea. (B,L,D)

  • DAY 5: 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’ll sail in the morning with the islands of Vulcano and Stromboli in view, anchoring for the afternoon at Lipari. Here we’ll 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’ll have dinner on deck as Sea Cloud cruises the 25 miles to Stromboli—and with a little luck, we’ll see some of the pyrotechnics of this active volcano. (B,L,D)

  • DAY 6: 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. 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. We dock in the port of Messina 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, we 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. We then return to Sea Cloud in the port of Messina. (B,L,D)

  • DAY 7: Siracusa

    Sail south to Siracusa, a city that once rivaled Athens in cultural and economic wealth. We’ll 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 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. (B,L,D)

  • DAY 8: At Sea

    After a few action-packed days, we take a full day for sailing along the south coast of Sicily. Join our expedition staff for talks on the Lido Deck, as the captain takes best advantage to work with winds of any directions 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 just enjoy the thrill of an extended sail on a historic square-rigged tall ship. (B,L,D)

  • DAY 9: Selinunte & Marsala

    Anchor in the fishing town of Mazara del Vallo and set out for a morning visit to the archaeological park of Selinunte. The giant columns, temples, stairways, and city walls are a delight for photographers and explorers of all interests—and the natural setting is spectacular. The site has some of the finest architecture of the ancient world. After a seaside lunch, we explore 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 Marsala’s most historic winery, Casa Florio, before returning to Sea Cloud in Mazara del Vallo. (B,L,D)

  • DAY 10: Agrigento/At Sea

    Our final call in Sicily 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. We return to Sea Cloud in Porto Empedocle and cast off for a relaxing afternoon under sail. (B,L,D)

  • DAY 11: Gozo, Malta/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’ll 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 Sea Cloud. This evening, we’ll celebrate our voyage with the Captain’s Farewell Cocktail Party and Dinner at sunset. (B,L,D)

Please note: All day-by-day breakdowns are a sampling of the places we intend to visit, conditions permitting.

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