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Voyage to Antiquity: Exploring Sicily and Malta

Mediterranean Sailing Cruise

Summary : As rich as their history is, these places aren't just monuments to the past. Their vibrant cultures, including their music and foods, have been exported all over the world, and their people have settled widely in other places. So in addition to an exploration, this voyage is in a sense a homecoming. Enjoy ample time sailing the Mediterranean, on the world’s most beautiful tall ship. Explore some of the world’s greatest Greco-Roman sites, along with towns and villages with vibrant life and culture.

Activities : Child-Friendly, Culture, Hiking


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Day 1

Depart on an overnight flight to Valetta, Malta.

Day 2
Valletta, Malta

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. Receive 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.

Day 3
Sailing / Gozo

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 a focus on the ancient megalithic temples of Ggantija, a World Heritage site. Older than both the pyramids and Stonehenge, the giant structures of Ggantija 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 the stars.

Day 4

Enjoy a full day for sailing, with your 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 spot on its comfortable teak decks. Join your expedition staff for talks on the Lido Deck, as the captain takes best advantage of the winds. You’ll have the first of your Sicilian wine tastings of the voyage this afternoon.

Day 5
Agrigento / Sailing

Your 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 6
Selinunte / Marsala

Anchoring at the fishing town of Mazara del Vallo for the day, 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, visit one of Marsala’s wineries for a tasting. Continue to Trapani to rejoin Sea Cloud.

Day 7
Erice / Sailing

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 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. 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 will feature a talk on the history of the legendary Sea Cloud, followed by an “open house” viewing of some of the original staterooms.

Day 8
Sailing / Cefalù

Adding sails in the morning, continue with on-board presentations and photography workshops. This afternoon, anchor off the stunning coastline promontory of Cefalù, whose name derives from the Greek word kefalo, 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. Explore the town on foot, and the more adventurous can hike to the top of 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.

Day 9
Sailing / 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. Set sail in the morning with the islands of Vulcano and Stromboli in view, anchoring for the afternoon at Lipari. 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 archaeological 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, have dinner on deck as Sea Cloud cruises the 25 miles to Stromboli, and with a little luck see some of the pyrotechnics of this active volcano.

Day 10
Strait Of Messina / Taormina

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. Drive up to the beautiful town of Taormina. 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 degli Schiavi. This phenomenal 18th-century home was the setting for many scenes in the Godfather films, and you’ll meet members of the family that owns it and explore the extensive buildings and grounds. Return after dinner to Sea Cloud, which has been at anchor under the watchful gaze of Mount Etna.

Day 11

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 the ship.

Day 12 – 13
Sailing the Ionian Sea

Leave the multitude of highlights of Sicily in your wake as you enjoy sailing aboard the Sea Cloud. 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, finish sampling Sicilian wines, and just enjoy the thrill of an extended sail on a historic square-rigged tall ship.

Day 14
Pylos / Nestor's Palace / Neo Kastro

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 15
Sailing and Exploring

The day is open to sail or explore, as the conditions allow. Your guides will assess the wind and sea conditions and the expedition as a whole to decide how best to use the final morning. Then set sail for the final afternoon in the Aegean Sea, bound like Theseus for Piraeus and Athens.

Day 16
Piraeus / Disembark / Home

Early this morning, arrive at the port of Piraeus, Athens’ gateway to the Aegean Sea. Disembark in the morning for transfers to the airport for flights home, or for the optional Athens extension.


This itinerary is subject to change. ExpeditionTrips is not responsible for itinerary changes.

Optional Pre-Voyage Extension: 2 Days from $1,090 per person
Malta: An island crossroads in the heart of the Mediterranean, Malta’s historic importance is tremendous. One group after another has conquered the archipelago, and left its indelible mark on Malta’s culture and architecture. Greeks, Phoenicians, Romans, Muslims, Sicily, Aragon, the Knights of St. John, Napoleon, and the British have all ruled Malta. Malta is today an independent country that is part of the European Union. Please contact ExpeditionTrips for details.

Optional Post-Voyage Extension: 2 Days from $1,390 per person
Athens: Venture straight to the heart of Ancient Greek culture. See the Acropolis on an early morning walk, visit renowned museums, see the landmarks of the city, and dine on regional specialties—all in the company of guides who weave the narrative of life of this ancient city. Please contact ExpeditionTrips for details.

Included: Accommodations aboard ship; meals indicated; services of expedition leader, historian, naturalist staff, and expert guides; port charges and service taxes. Subject to change without notice.

Not Included:
Air transportation; extensions; passport, visa, and immigration fees; some meals; baggage/accident/travel protection plan; items of a personal nature, such as alcoholic beverages, email, and laundry; gratuities to ship's crew at your discretion.

Photos: © Lindblad Expeditions, © Shutterstock

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