Circumnavigation of Sicily

Cruising Sicily
September 22, 2019
13 Days
Small-Ship Cruise
95 Guests
From $9,980


Based on the expeditionary nature of our trips, there may be ongoing enhancements to this itinerary.
Below please find the day-by-day itinerary for this expedition. Unless otherwise noted, daily excursion options are included in the cost of the trip. We do our best to adhere to the scheduled itinerary, but in the spirit of our expeditionary style of travel we may deviate slightly to take full advantage of encounters with the destination and its people, culture, and wildlife.

Sicily map

Depart USA

September 22

Board your independent flight to Valletta, Malta.

Valletta, Malta

September 23

Arrive in Malta this afternoon and transfer to our hotel with the remainder of the day at leisure. This evening, attend a welcome reception with dinner and overnight at our hotel.

Valletta / Embark Serenissima

September 24
Cruising Sicily

After breakfast, explore historic Valletta, Malta’s enchanting capital city built by the Knights of St. John in the 16th century. Visit the National Museum of Archaeology, the Grand Master’s Palace, St. John’s Co-Cathedral, and the Temple of Hagar Qim, a complex of monolithic edifices built between 3600 and 2500 BC. Embark the Serenissima this afternoon.

Pozzallo, Sicily / Ragusa

September 25

Take a drive through scenic countryside to the charming town of Ragusa, recognized by UNESCO for its outstanding Baroque architecture. Wander through the historic center, a tangle of alleys and plazas that tumble down a dramatic gorge, to view elegant palaces and elaborately decorated churches. After lunch at a local restaurant, head to a nearby farm to sample almonds and fresh ricotta. Return to Pozzallo for dinner aboard the ship.


September 26

This morning, enjoy a guided tour of Agrigento, a World Heritage Site. The exquisite architecture of the Valley of the Temples dates back to the 4th and 5th centuries BC and includes the Temple of Zeus—the largest Doric temple from Greek antiquity. Enjoy lunch at a local farmhouse before returning to the ship in the late afternoon. 

Trapani / Erice / Segesta / Marsala

September 27
Trapani, Sicily

Step ashore in the thriving fishing town of Trapani, then depart overland to visit Erice, a charming medieval village perched high on a mountain-top with stunning views of the Tyrrhenian Sea. Alternatively, visit the ruins of Segesta, once the center of the ancient Elymian civilization, and home to a magnificent Doric temple. Both groups will sample olive oil at a farm in Fontanasalsa, before returning to the ship for lunch. This afternoon, drive to Marsala for a walking tour. Make a stop at Cantine Florio, one of Sicily’s ancient wine estates, to enjoy local specialties accompanied by Marsala wines.

Palermo / Monreale

September 28
Palermo, Sicily

Palermo is famous for its jumbled and picturesque streets punctuated with ornate Baroque churches, domed Arab mosques, and Byzantine mosaics. Visit the impressive 12th-century Cathedral and the Palatine Chapel in the Norman castle; today the building serves as the seat of the Sicilian government. Highlights of your walking tour through the town center include the famous Ballaro food market, Massimo Theater, Quattro Canti, Town Hall, and Martorana Church. This afternoon, you are free to explore Palermo on your own, or join an optional guided tour of Monreale’s fabled Cathedral. Built in 1174 and hailed as Italy’s most beautiful Norman church, the interior is covered with mosaics, gold leaf, and stone intarsia.


September 29
Cefalu, Sicily

Situated on the northern coast, Cefalù is of Greek origin; its name, meaning “head,” derives from its position below a precipitous rocky headland. A walking tour includes the splendid Norman-Arab Cathedral, begun in 1131 and famous for its glittering Byzantine mosaics; a medieval wash-house; and the Osterio Magno, the 11th-century residence of King Ruggiero II. Lunch is a highlight today as you join a local chef at Tasca Lanza Estate who will teach you how to prepare traditional Sicilian dishes. There will also be time for wine sampling and a chance to explore the lovely grounds of the Estate, or to simply relax among your scenic surroundings.

Lipari, Aeolian Islands / Stromboli

September 30
Stromboli Volcano, Sicily

Take a walking tour through the center of Lipari to reach the impressive fort, built in 1556 upon the ruins of an ancient Greek acropolis. Within the fort walls you will find the superb Aeolian Archaeological Museum and the lovely Norman St. Bartolomeo Church. Return to the ship for an afternoon of cruising through the lovely Aeolian Islands en route to active Stromboli Volcano for sunset photos, with the chance to watch for the Stromboli “fireworks” as darkness falls.

Catania / Mt. Etna / Taormina

October 1
Taormina, Sicily

This morning, disembark in Catania and board coaches for an excursion to 9,500-foot-high Mt. Etna, Europe’s largest active volcano. Take a cable car up Etna’s pock-marked slopes, then continue in 4x4 vehicles to reach the main crater at 9,000 feet, with the opportunity for a short hike. In the afternoon, a walking tour of charming Taormina takes you to the 3rd-century Greco-Roman Theater, renowned for acoustic effects that make it a favorite concert venue to this day. Then take a stroll along the lively pedestrian-only Corso Umberto and explore its many narrow off-shooting lanes that lead to pretty piazzas lined with shops. 

Catania / Morgantina

October 2
Morgantina, Sicily

Today you have your choice of two tours. An inland drive takes you through a series of photogenic villages to Piazza Armerina, famous for its superb Roman mosaics in the Villa Romana del Casale. Enjoy lunch at a Sicilian restaurant near the Greek site of Morgantina, then tour the ruins and visit the small, but excellent Aidone Museum. Or, choose a city tour that visits the famous morning fish market in Catania’s town square where a colorful variety of local products are on display.  After lunch aboard the ship, or on your own in town, enjoy an afternoon at leisure to explore Catania on your own.

Syracuse / Ortygia

October 3
Syracuse, Sicily

Founded by the Corinthians in the 8th century BC, Syracuse was one of the most powerful Greek cities—defending its sovereignty against such rivals as Carthage, the Etruscans, and the Romans, who later overtook the city, followed by the Arabs. Begin at the Saint John Catacombs with their maze of underground passageways then drive to the Archaeological Park, a World Heritage Site. Highlights include the Roman Amphitheater of Augustus; the Ear of Dionysius, a grotto with an extraordinary echo; and the massive 15,000-seat Greek Theater. Return to the ship, at port in Ortygia, for lunch, before striking out for a walking tour of the old town. Highlights include the ruins of the 6th-century BC Apollo Temple—the oldest in Sicily—and the Piazza Duomo, built around the ancient Temple of Minerva (Athena). There will be time to explore the small food market, or enjoy free time on your own, before heading back to the ship. 

Valletta, Malta / Disembark / USA

October 4

Disembark in Valletta this morning and transfer to the airport for your independent homeward flight.