
A Circumnavigation of Sicily - with Smithsonian Journeys

Valletta - Valletta
Duration: 9 Days
Boats: Le-Bougainville | Le-Dumont-D-Urville
Sailing Date : Aug 29 2025 | Apr 11 2026 | May 05 2026
Itinerary

Day 1 - Valletta
The whole of the Maltese capital Valletta is UNESCO World Heritage listed and occupies a peninsula in the north-east of the island. From the fountain of Tritons to Saint-Elme fort, there are as many majestic streets as there are narrow staircase vennels to explore. The painted loggia and carved corbels on the tall houses will accompany you in your explorations, and you’ll rarely be bothered by traffic. You can visit the Grandmasters palace decorated with coats of arms and frescoes. Saint-John’s cathedral and the ramparts which have guarded the city since the 16th century are also among the most emblematic sites of the city. Arranged in terraces, the Barrakka Gardens will punctuate your promenade with a green and floral experience.

Day 2 - Porto Empedocle, Sicily
Huddled on the south-western coast of Sicily, Porto Empedocles bears the name of the philosopher Empedocles, who lived in the region in the 5th century BC. An age-old city offered up to sun and sea, this is your doorway to the exceptional archaeological site of Temple Valley, a high place of Greek civilisation listed as a UNESCO World Heritage site. You can admire the remains of many temples dedicated to Zeus, his wife Hera and Hephaestus. Make sure you take in the magnificent Italian countryside, with its olive orchards that cover the hillsides.
2 available excursions
Agrigento's Valley of Temples & Museum, Agrigento's Valley of Temples

Day 3- Tunis
At the crossroads of civilisations, the capital of Tunisia is rich in cultural discoveries. The ruins of Ancient Carthage, a UNESCO World Heritage Site and particularly well preserved, testify to the splendour of this city that was once Rome’s great rival. The hill of Byrsa, the former fortified citadel of the Phoenician port and one of the presumed burial places of Saint Louis who died there during the Eighth Crusade, offers spectacular views over the Gulf of Tunis. In the Bardo National Museum, you will be able to admire one of the world’s finest Roman mosaic collections, including the magnificent portrait of the poet Virgil.
4 available excursions
Bardo Museum & Ancient Carthage, Carthage, Sidi Bou Said, & the Medina of Tunis, Crafts, Cuisine, & Ancient Sites, Bardo Museum & the Medina of Tunis

Day 4 - Trapani, Sicily
Bathed in the cobalt waters of the Tyrrhenian sea, Trapani is the former port of the Greek city of Erice, boasting a privileged natural position in western Sicily. As you wander through its little streets, you will discover a secular cultural heritage, bearing witness to the many influences of civilisations that came here: San Lorenzo Cathedral, Maria Santissima Annunziata sanctuary, the fountain of Triton. On the shaded restaurant terraces, savour some fresh fish from the morning’s catch. Or else you can opt for a seafood couscous, a culinary legacy from their Arab neighbours.
3 available excursions
Medieval Erice and Ancient Segesta, Trapani & Marsala: History, Salt, and Wine, The Archaeology of Selinunte

Day 5 - Palermo, Sicily
Palermo is the guardian of the Sicilian soul. Many have been attracted to this city, the largest capital of the Italian islands. Phoenicians, Carthaginians, Romans, Byzantines, Arabs, Normans... Palermo is a rich culmination of so many cultural influences as seen in the Moorish designs on the cathedral, and the Byzantine mosaics of the Palatine chapel, which is itself housed within the precincts of the Norman palace. You will fall under the spell of the palaces, baroque splendours that grace the town with their obsolete beauty. It is thrilling to stumble upon one of those fabulous markets, high in colour, and headily picturesque.
3 available excursions
Churches of Palermo and Monreale, Cefalu, Palermo, Palazzo Conte Federico, & Sicilian Street Food

Day 6 - Lipari, Aeolian Islands
Of the seven Aeolian islands, this is the largest and the most populated. Lying off the north coast of Sicily, in the Tyrrhenian sea, Lipari is one of UNESCO’s marvellous World Heritage sites. Its lava stone quarries and obsidian flow of Rocce Rosse are indications of its volcanic nature. The town, the largest urban area in the whole archipelago, proudly houses its citadel and its castle, both rooted in Antiquity. If you head further into the centre, you’ll be surprised to come across a Norman cathedral, complete with a magnificent baroque façade.
2 available excursions
Nature & History: Highlights of Lipari, Aeolian Winemaking

Day 6 - Sailing in front of Stromboli
Like Ulysses during his Odyssey, you will have the opportunity to admire the Stromboli, the capricious volcano that looms over the Aeolian Islands. Its activity, uninterrupted for thousands of years, has earned it the nickname the “Lighthouse of the Mediterranean”.

Day 7 - Taormina, Sicily
Located on Sicily’s eastern coast, in the province of Messina, the seaside town of Taormina is Sicily’s Saint-Tropez, boasting heritage sites, secluded beaches and luxury shopping. You can visit its medieval centre, suspended 300 metres above sea level, where terraces offer a spectacular view of the Mediterranean Sea. Another vestige from its past are the ruins of the Greco-Roman theatre. This extremely well-preserved site attracts visitors who are fascinated by the natural beauty of the area which overlooks a turquoise bay.
3 available excursions
Mt. Etna & Benanti Winery, Taormina and its Greek Theater, Ancient Taormina & Sicilian Winery

Day 8 - Syracuse, Sicily
Its undulating rocky coastline, the endless sandy beaches, the menacing form of Mount Etna which surveys its island like a patriarch, the flowery gardens on the hillside... Sicily lays out its varied landscapes like a shopkeeper displays his wares. Described by Cicero as “the most beautiful city in the world”, Syracuse was one of the most prestigious cities in Sicily and at her height was even a rival for Athens. A central city of Ancient Greece, it was home to a succession of civilisations, each of which has left their mark. The blend of Arabic, Roman, Norman, Byzantine and Spanish cultures makes Syracuse a town that is extraordinarily rich in fragrances, colours and flavours.

Day 9 - Valletta
The whole of the Maltese capital Valletta is UNESCO World Heritage listed and occupies a peninsula in the north-east of the island. From the fountain of Tritons to Saint-Elme fort, there are as many majestic streets as there are narrow staircase vennels to explore. The painted loggia and carved corbels on the tall houses will accompany you in your explorations, and you’ll rarely be bothered by traffic. You can visit the Grandmasters palace decorated with coats of arms and frescoes. Saint-John’s cathedral and the ramparts which have guarded the city since the 16th century are also among the most emblematic sites of the city. Arranged in terraces, the Barrakka Gardens will punctuate your promenade with a green and floral experience.