Ancient civilizations converged and flourished along the shores of Sicily, leaving a legacy of artistic masterpieces and important archaeological sites. Aboard Sea Cloud II, discover the island’s rich history as you circumnavigate its idyllic shorelines, enhanced by colorful spring wildflowers.

Starting at: $6,990 * Price includes special offer Make a Reservation Ask Us A Question or Call 855-330-1542
 The Greek Theater of Sicily's Taormina  Sails on the <i>Sea Cloud II</i>  <i>Sea Cloud II</i> at full sail  The Temple of Segesta, Sicily  Cloisters of the Monreale Cathedral  Mosaic at Monreale Cathedral  The Palatine Chapel, Palermo  The Greek theater of Taormina with Mt. Etna in the background  The Baroque cathedral in Siracusa, built on the ruins of a Greek temple  The Greco-Roman Theater at Syracuse  Harbor scene in Valletta, Malta  Valletta harbor, Malta  St. Angelo Fort in Valletta, Malta

Sicily by Sea

Round-trip from Malta aboard Sea Cloud II

10 days from $6,990

Ancient civilizations converged and flourished along the shores of Sicily, leaving a legacy of artistic masterpieces and important archaeological sites. Aboard Sea Cloud II, discover the island’s rich history as you circumnavigate its idyllic shorelines, enhanced by colorful spring wildflowers.

or Call 855-330-1542


Ancient civilizations converged and flourished along the shores of Sicily, leaving a legacy of artistic masterpieces and important archaeological sites. Aboard Sea Cloud II, discover the island’s rich history as you circumnavigate its idyllic shorelines, enhanced by colorful spring wildflowers.

Highlights Include

  • Malta: Select from four full-day excursions focusing on Malta’s archaeology, military history, the Valletta harbor, or featured architecture. Board Sea Cloud II in the late afternoon and set sail for Sicily.
  • Segesta and Erice: Following a full day under sail, arrive on the west coast of Sicily. Stop to explore the Greek Doric temple of Segesta, then choose to see the hilltop fortress of Erice or savor a wine tasting in Marsala.
  • Palermo: The morning highlight showcases the Norman cathedral of Monreale and Cappella Palatina of Palermo, both featuring renowned Byzantine mosaics. Then choose from a wide variety of afternoon excursions.
  • Aeolian Islands: Discover the island of Lipari by foot, e-bike, or a drive, returning to the ship for lunch and afternoon swim. Enjoy sailing through the Strait of Messina at sunset.
  • Taormina: Tour the renowned Greek Theater, ride the cable car to the summit of Mt. Etna, or hike in Alcantara Gorge. Cruise to Syracuse in time for the evening passegiatta.
  • Syracuse: Explore the treasures of the Archaeological Park and the Old Town of Ortygia, including the Church of Santa Lucia with the famed Caravaggio painting. Visit a private palazzo as guests of the owner before cruising back to Malta.
  • The Sea Cloud II Experience: White sails billowing aloft three tall masts, a vision to behold. Nothing can top the experience of sailing aboard the square-rigger Sea Cloud II with her 23 sails all set by hand. Watch in awe as crew members climb the rigging to set the sails. Savor fine dining in the luxurious salon or on the open teak deck, enjoy engaging presentations and casual conversation in the piano lounge, and depending on your interests, discover the library, fitness studio, spa services, or swim platform. Yet you’ll also feel comfortable retiring to your cabin or suite—a spacious, stylish, and delightful retreat. See more information in the Tour Details tab. Our voyage will also host other leading cultural and educational institutions, which will add to the excitement and energy of the experience.


Day 1 & 2 – Depart U.S., Arrive in Valletta, Malta

Depart the U.S. on your transatlantic flight to Valletta. Transfer and check in to your centrally located hotel, overlooking Marsamxett Harbor. In the early evening meet your fellow travelers at a private welcome reception. (R)

Day 3 – Valletta / Embark Sea Cloud II

The entire city of Valletta is a World Heritage site, built by the Knights of St. John to defend against Ottoman invasions in the 16th century. Tour the icons of Malta from St John’s Cathedral, where Caravaggio’s masterpiece The Beheading of St. John the Baptist hangs, to Renzo Piano’s architectural works and sample Maltese cuisine over lunch in an historic palazzo. In the late afternoon board Sea Cloud II and gather on deck as the ship departs Valletta’s Grand Harbor. This deep natural harbor has been a safe refuge since ancient times. With views of Fort St. Angelo, Fort Ricasoli and the historic Three Cities on one side and the magnificent re-developed Pinto Vaults on the other, Malta’s Grand Harbor is one of the most beautiful harbors in the world. (B,L,D)

Day 4 – Full Day of Sailing

Sit back and watch skilled deckhands as they scale the masts that reach 180 feet high and set the sails on the finest hand-sailed square-rigger of our age. Also enjoy several presentations throughout the day plus savor free time to take advantage of the ship amenities. (B,L,D)

Day 5 – Trapani, Sicily (Segesta, Erice, and Marsala)

Begin your exploration of Sicily with a visit to Segesta one of the most important cities of the Elymians, an indigenous population of Sicily who also founded Erice. Visit the two main monuments, the well-preserved Doric Temple, thought to have been designed by an Athenian architect, and the semicircular theater, located on top of a nearby hill boasting wonderful views that made stage scenery unnecessary. Then, choose between an ascent to the hilltop medieval town of Erice, where an impressive Norman castle sits atop the ruins of a temple of Venus and tiny treasure-filled churches dot the cobbled alleyways, or travel to Marsala, an ancient seaside city famous for its wine, and visit Florio Winery, Marsala’s oldest winery, and delve into the winery’s history on a private tour complete with a lovely food and wine pairing.(B,L,D)

Day 6 – Monreale & Palermo

Today visit Monreale, home to a stunning 12th-century cathedral, that is both a national monument of Italy, as well as a World Heritage site and one of the greatest surviving examples of Norman architecture in the world. Continue on to the historic capital city of Palermo to marvel at its diverse architectural treasures, including the Norman-style Royal Palace and its dazzling Royal Chapel (Cappella Palatina), also a World Heritage site. Enjoy lunch sampling Sicilian street food, a centuries-old tradition in Palermo, in the city’s atmospheric Old Town. Spend the remainder of the afternoon exploring the narrow and lively streets of Old Palermo; a visit to Palazzo Abatellis, a medieval palace sensitively renovated by the architect Carlo Scarpa (1906-1978) as an art museum; or explore Palermo’s famed Archaeological Museum, which features priceless artifacts from Sicily’s major sites. (B,L,D)

Day 7 – Lipari, Aeolian Islands

Sail to the small volcanic island of Lipari, part of the Aeolian Islands, a World Heritage site. In some places, the island’s volcanic rock formations seem to resemble sculptures, and its cultural history stretches back 7,000 years. While ashore choose between an E-bike excursion through Lipari’s stunningly beautiful landscape; a drive around the perimeter of the entire island, with spectacular views of the other Aeolian volcanoes; or an in-depth walking tour of the town center with a visit to the Aeolian Archaeological Museum, offering an impressive collection of ancient artifacts from this volcanic group of islands. Return to the ship for lunch and an afternoon presentation as you sail. This evening gather on deck for a cocktail reception as the ship cruises by Stromboli, and with a little luck, see some of the pyrotechnics of this active volcano. (B,L,D)

Day 8 – Mt. Etna or Taormina

Arriving in the harbor below Taormina, spend the morning exploring this cliffhanging, old-world resort town, often compared to Positano and Èze, France. Our local guide leads us through the charming market, buzzing shops and cafés on the fashionable pedestrian-only Corso Umberto to the Ancient Greek theater, home to performances for two thousand years. Theater seats look out over dramatic cliffs to the shimmering Ionian Sea and a coastline that is visible for 30 miles. Weather permitting, choose to forgo Taormina for a trip to Mt. Etna, ascending the slopes via cable car for stunning views from the top of Europe's largest active volcano (Active). Return to the ship for lunch and set sail for Siracusa arriving in time to join Sicilians for La Passeggiata, the Italian tradition of taking a walk in the evening. There is no better place to experience this Italian social ritual than in the beautifully lit streets of Siracusa’s historic center. (B,L,D)

Day 9 – Syracuse

Once a powerful threat to the hegemony of Athens, Siracusa was founded around 734 B.C. by Greek Corinthians. Because of its strategic location, it was conquered and ruled by Romans, Saracens, Byzantines, Normans, and Ottomans, who left a combined legacy of archaeological treasures that have earned Siracusa as a World Heritage site. Tour the expansive archaeological park home to the stunning Greek Theater, where Aeschylus’ plays were performed, as well as the Roman Amphitheater that combine to make this one of the greatest archaeological sites in all of Italy. Continue to the island of Ortygia, which separates Syracuse’s two harbors, to take in the sights and smells of the bustling food market, before strolling through the beautiful alleyways and piazzas to the Piazza del Duomo, home to the city’s monumental cathedral built within and around a pagan temple, whose Doric columns are still visible. From there, attend a private opening of the Santa Lucia alla Badia church, dedicated to the city's patron saint, St Lucy, martyred in Syracuse during the reign of the Roman emperor Diocletian. The church is home to Caravaggio's arresting masterpiece, Seppellimento di Santa Lucia (Burial of St Lucy, 1609). In a nearby palazzo dating back to the Middle Ages, enjoy a wine tasting in ta private 18th-century Sicilian nobleman whose family has been making wine since 1734 and view the family's collection of etchings of Siracusa. (B,L,D)

Day 10 – Valletta, Malta / Home

Gather on deck this morning as the Sea Cloud II returns to Valletta’s spectacular Grand Harbor. Following breakfast, prepare to disembark the Sea Cloud II for flights home. (B)

Included meals are denoted as follows: Breakfast (B), Lunch (L), Reception (R), Dinner (D)