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Relax in beautiful Sicily

Sicily & Malta

Example 11 Day Cruise aboard Sea Cloud
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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. We’ll visit no fewer than five UNESCO World Heritage Sites: Agrigento, Siracusa, the Aeolian Islands, the city of Valletta, Malta’s megalithic temples; and we’ll have views of a sixth, Mount Etna.
Naples at Sunset, ItalyCoast of Ortigia island at city of SyracuseAn abandoned theatre in Taormina, Sicily Explore Malta's capitalRelax in beautiful Sicily
  • Sail the shimmering waters of the Mediterranean
  • Explore enchanting piazzas and alleyways of picturesque towns from Lipari
  • Visit UNESCO World Heritage Sites, from Greco-Roman ruins in
  • Experience Sicily’s unique cuisine at a wine tasting in Marsala
Trip Type:
  • Small Ship
Activity Level: Relaxed

Full Itinerary

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Day 1: Naples, Italy | Embark

Arrive in Naples. Board the legendary Sea Cloud and cast off from Naples’ harbor. Gather for a welcome cocktail as we pass the island of Capri’s rugged coast and enter the Tyrrhenian Sea. 

Day 2: At Sea

  • Ship
  • 1 Breakfast, 1 Lunch, 1 Dinner
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.

Day 3: Erice | At Sea

  • Ship
  • 1 Breakfast, 1 Lunch, 1 Dinner
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. 

Day 4: Lipari | Stromboli

  • Ship
  • 1 Breakfast, 1 Lunch, 1 Dinner
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.

Day 5: Strait of Messina | Taormina

  • Ship
  • 1 Breakfast, 1 Lunch, 1 Dinner
Enjoy breakfast on the 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.

Day 6: Siracusa

  • Ship
  • 1 Breakfast, 1 Lunch, 1 Dinner
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.

Day 7: At Sea

  • Ship
  • 1 Breakfast, 1 Lunch, 1 Dinner
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.

Day 8: Selinunte & Marsala

  • Ship
  • 1 Breakfast, 1 Lunch, 1 Dinner
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.

Day 9: Agrigento | At Sea

  • Ship
  • 1 Breakfast, 1 Lunch, 1 Dinner
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.

Day 10: Gozo, Malta | At Sea

  • Ship
  • 1 Breakfast, 1 Lunch, 1 Dinner
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. 

Day 11: Valletta | Disembark

  • 1 Breakfast
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. You’ll want to be on deck with your camera as we make our final approach beneath the city’s 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. (B)


Sea Cloud

Sea Cloud Ship
Sea Cloud's beautiful interior.
Relax on the sun deck of the Sea Cloud.

Dates & Prices

My Preferred Start Date

Per person starting at
Relax in the Sea Cloud's comfortable cabins.
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Category 1
Cabins 28-29 on Promenade Deck. Cabins have two single beds, a window and private bath facilities.
Sea Cloud's Category 1S Cabin.
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Category 1S
Cabins 16-17, Promenade Deck. Upper and lower single beds, window. These cabins once housed the ship's officers.
Relax in the Sea Cloud's comfortable cabins.
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Category 2
Cabins 18-25 on the Promenade Deck. Cabins have two single beds, a window and private bath facilities.
Relax in the Sea Cloud's comfortable cabins.
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Category 3
Cabins 32-37 on Captain's Deck. Cabins have two single beds, a window and private bath facilities.
Sea Cloud's Category 1-4 Cabins.
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Category 4
Cabins 30-31, Captain's Deck. Cabins have a queen bed, forward-facing window and private bath facilities.
Sea Cloud's Category B Cabin.
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Category B
Deluxe Cabins 3-10, Main Deck. Large original cabins have a mix of bed types and decor motifs. All have portholes.
Sea Cloud's Category A Cabin.
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Category A
Deluxe Cabins 3-10, Main Deck. Large original cabins have a mix of bed types and decor motifs. All have portholes.
Sea Cloud's Owner's Suite.
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Category OS
Original owners suites 1-2, Main Deck. King sized beds, grand marble bathrooms with bathtubs.


Aboard ship
  • All meals and non-alcoholic beverages*
  • Cappuccinos, lattes & filtered water
  • 24-hour coffee, tea & soda on demand 
  • Hors d’oeuvres & snacks during Recap
  • Fitness center or exercise equipment, depending on the ship
  • Fully stocked library, and other gracious public spaces
  • The guidance and company of our expedition staff
  • The services of a physician on certain ships/destinations
  • Meals on land, as indicated in the itinerary
  • Sightseeing & entrance fees
  • Special access permits, park fees, port taxes
  • Transfers to and from group flights
  • The expertise of our expedition staff
  • All excursions
  • Zodiac & kayak explorations
  • Snorkeling, including wetsuits, masks, fins & snorkel where relevant
  • Presentations and guest speakers in the lounge
  • International and internal airfare
Pre- and post-expedition
  • Additional hotel nights
  • Private transfers
  • Travel Protection Plan
  • Passport, visa, and immigration fees
  • Expedition extensions
  • Gratuities
Aboard ship
  • Alcoholic beverages 
  • Spa treatments
  • Gratuities 
  • Laundry
  • Gift shop items and any other items of personal nature

Rates are capacity-controlled and are subject to change without notice.



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