Small Groups: Never more than 10-16 travelers—guaranteed!
An Italian island with 3,000 years of history, Sicily was once home to a Greek colony, a Roman province, an Arab emirate, a Norman kingdom, and more. Traces of these ancient conquerors can still be found in Sicily’s rich and diverse variety of ancient ruins, elegant architecture, and gastronomic delights. Experience Sicily’s full enchantment on a journey from the bustling streets of Palermo and ancient Greek temples of Agrigento to the Baroque beauty of Ragusa and Catania. Hear the rumbling groans of Mt. Etna, witness the splendor of palazzi and villas, visit quaint fishing villages, and discover the island’s rural authenticity with a night in an agriturismo—a traditional Sicilian farmhouse. Meet the friendly—and fiercely proud—Sicilian people and immerse yourself in the island’s landscapes, history, and culture. Just be sure to bring an open mind—and a hearty appetite.
Fly overnight from the U.S. to Palermo, Sicily.
Today, arrive in Sicily. After you are met and transferred to your hotel, you'll enjoy an orientation walk and Welcome Drink with your fellow travelers and Trip Leader. You'll also meet those who traveled on our optional Puglia: Italy's Undiscovered Heel extension. Dinner is at a local restaurant tonight.
This morning, we enjoy breakfast at the hotel before departing for our first excursion in the province of Palermo: Monreale, where we will enjoy a guided visit. We'll view the town’s 12th-century Norman Cathedral, which sits in the hills overlooking Palermo. See Byzantine art come to life within the cathedral’s nave, where nearly every surface is covered with intricately-detailed mosaics depicting biblical scenes in rich colors and gold filigree. Then we explore Kalsa, Palermo's historic Arab Quarter, as we witness modern life here on a walk through town. We’ll discover the quarter with all our senses as we walk past botanical gardens, Baroque churches, and savor the local street food here—some of which originated from Africa’s Mediterranean coast.
After lunch, you'll have some time at leisure to make your own discoveries, which our Trip Leader may help you identify. We meet up again later in the afternoon for an exploration of the 14th-century palace turned tribunal for the Inquisition in Sicily from 1601-1782. A walk through the prisoner cells reveals graffiti-marked walls—a chilling reminder of darker period in Palermo’s history.
Dinner is on your own tonight.
After breakfast, you may wish to join a half-day optional tour to Cefalù & Castelbuono on Sicily’s northern coast. Cefalù, which takes its name from the Greek word meaning “cape,” is a small town situated between a natural bay and towering granite cliff called La Rocca. Built for the Norman King, Roger II, the picturesque historic town features a “Sicilian Romanesque” cathedral that began construction in 1131. After exploring Cefalù, we’ll visit Castelbuono, a medieval town in the Madonie Mountains. Enjoy lunch at an agriturismo in Castelbuono, and view the battlements and towers of the town’s imposing 14th-century castle. Then, return to Palermo in early afternoon.
Travelers choosing not to join our optional tour will enjoy a day at leisure in Palermo. The city’s strategic position in the middle of the Mediterranean has led to past filled with a regular succession of invaders, from Phoenicians, Carthaginians, Greeks, and Romans, to Normans, Swabians, French and Spanish Bourbons, and more. This helps to explain the city’s eclectic mix of architectural styles—although the 17th- and 18th-century Baroque period has left the most visible mark on Palermo’s civic and religious structures. Intense rebuilding after heavy bombing during World War II has also contributed to the city’s chaotic beauty. Depending on your interests, your Trip Leader can offer suggestions on where to find the most interesting museums, medieval churches, Byzantine mosaics, or bustling street markets for an authentic taste of local life. Or if you’re brave, you may even wish to visit the mummified cadavers at Palermo’s Catacombe dei Cappucini.
Enjoy dinner together at a local restaurant this evening.
After breakfast, we depart for Mazara del Vallo, one of Italy’s premier deep-sea fishing ports. En route, we stop in Marsala, the port town in the westernmost part of the island that is home to Italy’s classic fortified wine—and the site of the famous landing by Garibaldi, who arrived here in 1860 with his thousand-strong army to begin the unification of Italy. With its shallow coastal waters, the region between Trapani and Marsala is also renowned for its ancient tradition of sea-salt production, and it is still harvested just as it was in Carthaginian times utilizing centuries-old windmills. We’ll walk through this diverse landscape, observing the flourishing variety of wildlife of the salt pans to the small island of Mothya. Some 2,700 years ago, the Phoenicians built a settlement here. We’ll tour the ancient island fortress and enjoy a picnic lunch amid the peaceful and historic surroundings before returning to Marsala.
Marsala’s historic roots stretch back to the ancient Carthaginians, followed by the Romans. In AD 830, the town was conquered by the Arabs, who paid homage to its strategic importance by naming it “Marsa Allah,” which means “Port of God.” A walking tour of Marsala’s historic center will include the elegant Piazza della Repubblica, home to a series of stately Baroque buildings and the imposing 17th-century Marsala Cathedral.
Later this afternoon, we continue to Mazara, where we’ll check into our hotel and enjoy dinner together this evening.
Breakfast is followed by a walking tour of Mazara. We’ll see its impressive Duomo and visit a museum built to house the famous “Dancing Satyr,” a mysterious Greek bronze statue brought up by local fishermen in 1998 after resting on the seabed for 2,000 years. We’ll also stop at San Francesco, a church and convent that originated during the Middle Ages and was rebuilt in the Baroque style in 1680.
After lunch on our own, perhaps you’ll wish take a stroll along the Lungomare Mazzini, the pleasant sea-front promenade, shaded by magnolia trees. Then, we’ll take a short drive to Erice, a wonderfully preserved medieval town that towers over Sicily’s western coast. We’ll enjoy breathtaking views over Trapani and the Tyrrhenian Sea, followed by an included dinner at a local restaurant.
Today begins with a hearty breakfast, followed by an inland excursion to Partanna, an ancient Sicilian town whose historic structures were badly damaged by an earthquake in 1968. We will hike in an outlying valley to admire the region’s natural beauty, which retains many archaeological traces of ancient settlements, followed by a picnic lunch.
This afternoon, we’ll visit Mazara’s historic Kasbah quarter, where some 3,000 Tunisians and other Maghreb Arabs live and work. Here, we’ll learn about the intermingling of Sicilian and Arab culture and the co-existence of Muslim and Christian faiths during an enlightening discussion. Afterwards, we’ll meet with a local Arab family who will show us how to cook traditional couscous. Dinner is included this evening.
After breakfast, we depart for Piazza Armerina. Along the way, we stop at the Valley of Temples, situated just outside the city of Agrigento. Agrigento was once the Greek city of Akragas, one of the most culturally advanced cities of the ancient world. In the Valley of Temples, we’ll view the stunning archaeological remains of eight Greek temples, built between 510 and 430 BC.
After lunch in a local restaurant in Agrigento, we continue our journey deep into the Sicilian hinterlands to Piazza Armerina. Upon arrival at our agriturismo (a traditional farm house sanctioned for lodging by the Italian government), we’ll visit its wine cellar for a tasting, followed by a sumptuous dinner at the farm’s restaurant featuring locally grown cuisine.
Following breakfast, we depart for Villa Romana del Casale, home to the ruins of an extraordinary Roman villa. Constructed in the middle of the 4th century AD as a hunting lodge, the villa was covered by a landslide in the 12th century. Twentieth-century excavations have revealed some of the finest examples of Roman mosaics in all of Europe, with scenes ranging from Homeric escapades to depictions of daily life. The villa is now a UNESCO World Heritage Site.
After lunch at a local restaurant, we journey to Ragusa. After Ragusa was leveled by an earthquake in 1693, wealthier members of the population decided to build their new town higher up a cliff, while the rest of the inhabitants rebuilt on the original site, at the bottom of a gorge. The two distinct towns remained separated until 1926, when the higher and lower sections became one, and now a jumble of homes and churches cling to the walls of the steep ravine that divides them. Upon arrival, we’ll first explore Upper Town—Ragusa Superiore—noted for the extravagant Sicilian Baroque architecture of the Cathedral of San Giovanni Battista and breathtaking views of the surrounding countryside. Dinner is on your own this evening.
This morning, our discoveries focus on the Baroque splendor of Ragusa Ibla, one of Sicily’s best-preserved old towns, and a UNESCO World Heritage Site. We’ll view numerous structures ornately decorated in the Baroque style with elaborate balconies. A highlight is the 18th-century Duomo di San Giorgio, set in the center of Ibla, with a neo-classical dome added in 1820. After lunch on your own in Ibla, you have leisure time to explore its picturesque alleys and stairways. Perhaps you’ll sample a treat from Gelati DiVini, a local shop specializing in delicious wine-flavored ice creams.
Later this afternoon, we depart to the neighboring town of Modica, part of the Val di Noto UNESCO World Heritage Site. Like Ragusa, Modica was largely rebuilt in the Sicilian Baroque style after the 1693 earthquake—and is also divided into upper and lower sections, connected by numerous flights of steps. We’ll walk the cobblestone streets to admire its various buildings, considered to be among the most beautiful architecture in Sicily. Enjoy dinner at a local restaurant this evening.
After breakfast at our hotel, we journey outside of Ragusa to the Vendicari Nature Reserve, a government-protected reserve along Sicily’s southeastern coast. Vendicari consists of a scenic mix of lagoons (pantano), sand dunes, and stretches of sandy beaches and rocky coastlines. After some hiking in this marshland oasis that is temporary home to thousands of migratory birds heading to or from Africa, we’ll head to Marzamemi. This picturesque fishing village is home to the island’s original tonnara, a tuna processing plant begun by Arabs in the tenth century. The village is still known for its artisanal fishing products—including a dried tuna roe called bottarga—and you can enjoy lunch on your own here while watching the colorful wooden boats bobbing in the harbor. After returning to Ragusa, dinner is on your own this evening.
After breakfast at our hotel, we depart for Syracuse, known as the birthplace of the famed mathematician Archimedes and as one of the most powerful ports of the ancient Mediterranean world. At 2,700 years old, Syracuse boasts a rich and storied history—evident today in the city’s Greek, Roman, and Baroque architecture, which has helped earn Syracuse UNESCO World Heritage Site designation. While in Syracuse, we’ll tour its famous Archeological Park, situated in the northwest corner of the town. Here, we’ll admire an impressive collection of well-preserved Greek and Roman relics, including the 5th-century BC Greek theater that once held 15,000 spectators and the Roman amphitheater, where gladiators and wild animals clashed in the 3rd Century AD.
From here, we’ll continue to the nearby island of Ortigia, where an enticing blend of architectural styles awaits. Wander among Greek and Roman ruins, Medieval Norman structures, and Baroque buildings. The island also boasts the fountain of Arethusa, the Temple of Apollo, and the Piazza del Duomo, the lovely pedestrian square that serves as the heart of Ortigia. After our discoveries on foot, we’re treated to a new perspective of Syracuse, as we embark upon a sail of its sparkling bay. We’ll enjoy lunch onboard as we take in the views.
Then we continue to Catania, where you’ll dine on your own this evening.
Breakfast this morning is followed by a guided tour of Catania, a vibrant city perched on the edge of the Ionian Sea. Founded in the 8th century BC, Catania was once among Italy’s most important cultural centers, particularly in the Renaissance period. Sicily’s first university opened here in 1434, and Catania’s tradition of education and industry continues to thrive today. We’ll visit the local WWII Museum, dedicated to the Allied landing on the southern coast of Sicily, as well as the local public fish market, where an array of sights and sounds (and seafood!) delight. Our tour concludes with a stroll along Via Crociferi, a scenic passage laced with churches, monasteries, and private homes.
After lunch on your own, you’ll enjoy time at leisure in Catania. Or perhaps you’ll choose to join our optional Taormina tour. Hillside Taormina invites with its scenic beaches and breathtaking views of the Ionian Sea, as well as its impressive Greek amphitheater, one of the most highly regarded ruins in Sicily. We’ll tour this site, and the historic town, before enjoying dinner at a local restaurant.
After breakfast at our hotel, we journey to the quaint alpine town of Linguaglossa, situated on the northern slope of Mount Etna. The tallest active volcano in Europe and the highest mountain in Italy south of the Alps, Mount Etna soars to a height of more than 10,000 feet. It’s also one of the most active volcanoes in the world, and its rich volcanic soil brings abundant vineyards and orchards to Etna’s slopes. From Linguaglossa, we’ll travel by donkey to one of Etna’s fascinating “lava caves,” formed by lava that cools and solidifies in a cavern-like formation. In all of Europe, such caves can only be in Iceland and here on Mount Etna.
After disembarking our donkeys, we’ll enjoy lunch in a local chalet. Then we’ll transfer back to Catania for time at leisure before gathering again this evening. We’ll toast our adventure over a Farewell Drink at the hotel, followed by a Farewell Dinner at a local restaurant.
We depart our hotel this morning and transfer to the airport for our flight home. Or, begin our Calabria: Southern Italy's Heartland extension.