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Visit the Cathedral of Palmero on your small ship cruise around Sicily

Voyage to Antiquity: Exploring Sicily and Malta

Exploring Sicily and Malta - Example 15 Day Cruise aboard Sea Cloud (LI)
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Embark on a new, singular expedition, so multifaceted, so rich in experience, and extraordinary, that it is sure to be remembered as one of the most remarkable journeys you’ve ever taken. Sailing aboard the Sea Cloud for 16 days, the most beautiful sailing vessel in the world, begin in Malta and focus on the island of Sicily, taking in its many aspects. There's a treasure trove of some of the world’s greatest ancient places. Visit no fewer than five UNESCO World Heritage Sites: the city of Valletta, Malta’s megalithic temples, Agrigento, Siracusa, and the Aeolian Islands, and take in views of a sixth, Mt. Etna. Conclude in the Greek capital of Athens, with opportunities for still further exploration.

Day-by-Day Summary

Day 1 : Valletta, Malta | Embark
Day 2 : Sailing | Gozo
Day 3 : Sailing
Day 4 : Agrigento | Sailing
Day 5 : Selinunte and Marsala
Day 6 : Erice | Sailing
Day 7 : Sailing | Cefalù
Day 8 : Sailing | Lipari | Stromboli
Day 9 : Strait Of Messina | Taormina
Day 10 : Siracusa
Days 11-12 : Sailing the Ionian Sea
Day 13 : Pylos | Nestor's Palace and Neo Kastro
Day 14 : Sailing and Exploring
Day 15 : Piraeus | Disembark


  • Explore some of the world’s greatest Greco-Roman sites and vibrant culture
  • Discover five UNESCO World Heritage sites, such as the city of Valletta
  • Enjoy Sicily’s celebrated foods, wines, herbs, olive oils, and music
  • Spend exhilarating time at sea under sail on the historic 4-masted Sea Cloud


Sea Cloud (LI)

Places Visited


Trip Type

  • Small Ship

Activity Level


Trip Snapshots

Visit the Cathedral of Palmero on your small ship cruise around Sicily The impressive city of Valletta, Malta Sicilian landscape in the early evening An abandoned theatre in Taormina, Sicily Ancient ruins in Athens

Day 1 Valletta, Malta | Embark

Arrive in Valletta, the capital of the Republic of Malta, a nation of Mediterranean islands that has had extraordinary importance throughout recorded history because of its strategic location, with myriad rulers and influences. It is today part of the European Union. You’ll have a short orientation in Valletta and its grand fortification of Fort St. Elmo, including an outstanding multimedia introduction at “The Malta Experience.” Embark Sea Cloud in the late afternoon. The ship will remain docked through the night, and there will be an evening shuttle the short distance to town, if you'd like to explore Valletta further during the evening. (D)

Day 2 Sailing | Gozo

  • Ship
  • 1 Breakfast, 1 Lunch, 1 Dinner
Sea Cloud casts off at sunrise to pass under the limestone bastions of Fort St. Elmo in the first light. Sea Cloud’s sailors then go aloft to set the sails, as you enjoy the magnificence of true square-rig sailing. This afternoon visit Malta’s second island, Gozo, with our focus on the ancient megalithic temples of Ġgantija, a World Heritage site. Older than both the pyramids and Stonehenge, the giant structures of Ġgantija were built by civilizations that thrived here more than 5,000 years ago. This evening meet the Captain and the ship’s officers for Sea Cloud’s welcome cocktail party and dinner, under a full moon. 

Day 3 Sailing

  • Ship
  • 1 Breakfast, 1 Lunch, 1 Dinner
Have the full day for sailing, with our Expedition Leader giving a “play-by-play” description of the sail activity and maneuvers on the decks of Sea Cloud. Take time to get familiar with Sea Cloud’s four masts and 29 sails, and find your favorite spots on her comfortable teak decks. Join our expedition staff for talks on the Lido Deck, as the captain takes best advantage of the winds. You’ll have the first of our Sicilian wine tastings of the voyage this afternoon. 

Day 4 Agrigento | Sailing

  • Ship
  • 1 Breakfast, 1 Lunch, 1 Dinner
Our first call in Sicily is devoted to Agrigento’s Valley of the Temples, a UNESCO World Heritage site that is a collection of some of the most magnificent Greco-Roman temples of antiquity. Founded in the 6th century BC by the Greeks, the area was subsequently ruled by Romans, Byzantines, Arabs and Normans. Its temples are monumental and extraordinarily beautiful. Return to Sea Cloud in Porto Empedocle, and cast off for a relaxing afternoon under sail. 

Day 5 Selinunte and Marsala

  • Ship
  • 1 Breakfast, 1 Lunch, 1 Dinner
Anchoring at the fishing town of Mazara del Vallo, make 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. In the afternoon, 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. After seeing these places, have a visit and tasting at one of Marsala’s wineries. Continue to Trapani, where you rejoin Sea Cloud

Day 6 Erice | Sailing

  • Ship
  • 1 Breakfast, 1 Lunch, 1 Dinner
After Sea Cloud docks at the regional hub of Trapani, depart this morning up nearby Mount Erice to the intriguing medieval town of Erice. Perched 750 meters above Trapani and Sicily’s western coast, both the walled town and the views are unforgettable. It’s a place full of ancient history and also a vital, living town. You’ll explore Erice with local guides and also have time to wander on your own, before you reunite at the renowned pasticceria of Maria Grammatico for coffee and pastries.
The deck crew heads back 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. This evening we’ll feature a talk on the history of the legendary Sea Cloud, followed by an “open house” viewing of some of the original staterooms. 

Day 7 Sailing | Cefalù

  • Ship
  • 1 Breakfast, 1 Lunch, 1 Dinner
Adding sails in the morning, continue with our on-board presentations and photography workshops. This afternoon anchor off the stunning coastline promontory of Cefalù, whose name derives from the Greek wordkefalo, or “head.” This is one of Sicily’s most beautiful towns, dominated by the 12th-century Norman cathedral with the headland rock La Rocca as its backdrop. You’ll explore the town on foot, and the more adventurous can hike to the top of 278-meter-high La Rocca for astonishing views over the town and the sea. Sea Cloud remains anchored at Cefalù through the evening, so you can return to this beautiful town at night, or even dine ashore if you wish. 

Day 8 Sailing | 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. Set sails in the morning with the islands of Vulcano and Stromboli in view, anchoring for the afternoon at Lipari. Here you’ll go ashore for a drive around the perimeter of the entire island, with spectacular views of the other Aeolian volcanoes, before returning to the main town. Visit the small but surprising archeological museum that has an extensive collection of Neolithic artifacts made from the local obsidian, which was also the foundation of the island’s prosperity during the Greco-Roman era. This evening, you’ll have dinner on deck as Sea Cloud cruises the 25 miles to Stromboli, and with a little luck you’ll see some of the pyrotechnics of this active volcano. 

Day 9 Strait Of Messina | Taormina

  • Ship
  • 1 Breakfast, 1 Lunch, 1 Dinner
In the early hours of the morning, pass through the narrow Strait of Messina, which separates Sicily from the “boot” of Italy. It’s the purported location of Homer’s monsters Scylla and Charybdis, the rock and the hard place through which Odysseus had to sail. Then drive up to the intoxicatingly beautiful town of Taormina, perched 250 meters above. With Mount Etna dominating to the south, this 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 BC.
This evening, a special treat: a private dinner at a privately owned castle, the Castello degliSchiavi. This phenomenal 18th-century home was the setting for many scenes in the Godfather films, and you’ll meet members of the family that own it and explore the extensive buildings and grounds. Return after dinner to the Sea Cloud, which has been at anchor under the watchful gaze of Mount Etna.

Day 10 Siracusa

  • Ship
  • 1 Breakfast, 1 Lunch, 1 Dinner
Siracusa was the great rival to Athens, and its archaeological park features one of the largest theaters of antiquity. Its 15,000 seats are hewn out of bedrock, and the theater is still in use today. Also visit the nearby limestone quarry, the cave of “Dionysus’ Ear,” and the Roman amphitheater before returning to Sea Cloud for lunch. The afternoon features a walk through the medieval island town of Ortygia. The town is magical, with numerous little piazzas and narrow alleys, but the main feature is the Duomo, or Cathedral, which was built from the ruins of the ancient Temple of Athena. The history of Sicily can be told in the walls of this incredible construction. Ortygia is at its best in the evening, so you might want to have a Sicilian pizza in town tonight, or return for a walk after dinner aboard ship.

Day 11-12 Sailing the Ionian Sea

  • Ship
  • 2 Breakfasts, 2 Lunches, 2 Dinners
Leave the multitude of highlights of Sicily in your wake as we enjoy Sea Cloud doing what she does best: sail. These two days have plenty of time built in to work with winds of any directions for optimal sailing, and with some luck you’ll have westerly winds for an overnight sail too. Aboard Sea Cloud there will be time to catch up on journals, photo reviews, questions, to finish sampling Sicilian wines, and just enjoy the thrill of an extended sail on a historic square-rigged tall ship.

Day 13 Pylos | Nestor's Palace and Neo Kastro

  • Ship
  • 1 Breakfast, 1 Lunch, 1 Dinner
Today arrive at the other end of the Ionian Sea, at the Greek Peloponnesian port of Pylos. Visit the exceptionally well-preserved Palace of Nestor, the king of Pylos who is prominently mentioned in Homer's Iliad and Odyssey. The palace dates from the 13th century BC.  In the afternoon walk to Neo Kastro, an impressive 16th-century Turkish castle, with time to explore. 

Day 14 Sailing and Exploring

  • 1 Breakfast, 1 Lunch, 116 Dinners
We will leave this day open to sail or explore, as the conditions suggest. We’ll assess the wind and sea conditions and the expedition as a whole to decide how best to use our final morning. We’ll then set sail for the final afternoon in the Aegean Sea, bound like Theseus for Piraeus and Athens. 

Day 15 Piraeus | Disembark

  • 1 Breakfast
Early this morning arrive at the port of Piraeus, Athens’ gateway to the Aegean Sea. You disembark in the morning for transfers to the airport for flights home.

Sea Cloud (LI)

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.


Included in Cost:
- Accommodations aboard ship
- Meals indicated
- Excursions
- Services of expedition leader historian & naturalist staff and expert guides
- All port charges and service taxes.

Not Included:
- Air transportation
- Extensions
- Passport, visa, immigration fees
- Meals not indicated
- Travel protection plan
- Items of a personal nature such as e-mail, laundry.
Payment & Cancellation Policies
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Our guide and driver were very good with their knowledge and were very helpful with our questions. It was a very pleasant visit that would have been impossible to do on our own. Hotels and restaurants were fantastic. The special places we got to go to, like the kitchens, were great. Enjoyed the entire trip!
Meyer Smolen

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