Traveling in Sicily is to discover an Italian island with more than 3,000 years of history. Once home to a Greek colony, a Roman province, an Arab emirate, a Norman kingdom, and more, traces of ancient conquerors can still be found in Sicily’s well-preserved ruins, elegant architecture, and gastronomic delights. Experience the isle's full enchantment on a journey from the bustling streets of Palermo and striking 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 Sicily's rural authenticity with a night in an agriturismo—a traditional farmhouse. Meet the friendly—and fiercely proud—Sicilian people and immerse yourself in its landscapes, history, and culture. Just be sure to bring an open mind—and a hearty appetite.
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For many years, the region of Puglia—commonly referred to as the “heel to Italy’s boot”—has been frequented only by sojourning Italians seeking sand and sun. Discover the full range of Puglia’s hidden treasures, from the Baroque beauty of Lecce and fortified island town of Gallipoli to the unique conical-roofed homes of Alberobello—and explore an unspoiled region where few American travelers have been before.View Extension Itinerary
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 meet your fellow travelers and Trip Leader. You'll also meet those who traveled on our optional Puglia: Italy's Undiscovered Heel extension. Enjoy a Welcome "finger food party" at a local wine bar tonight.
After breakfast at our hotel, we'll set off for a visit to a traditional market and enjoy a walking tour of Palermo followed by a visit to a local market where we can sample some traditional Sicilian street food. Then, after lunch on your own, you'll have some time at leisure to make your own discoveries, which our Trip Leader may help you identify.
We'll regroup later in the afternoon for a visit to Santa Chiara, an oratory that provides an after-school program for the youth in this very poor neighborhood populated by locals and immigrants from abandoning their studies and getting involved in illegal activities. Santa Chiara is also supported by Grand Circle Foundation. After our visit, we'll enjoy dinner at a local restaurant.
After breakfast, you may wish to join a full-day optional tour to Castelbuono & Cefalù on Sicily's northern coast. First we'll visit Castelbuono, a medieval town in the Madonie Mountains. Here, you'll view the battlements and towers of the town’s imposing 14th-century castle and enjoy lunch at a local restaurant. We continue to Cefalù, which takes its name from the Greek word meaning “cape.” This small town is 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. We return to Palermo in the late 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.
Later this afternoon, we'll gather for an enlightening discussion about the Sicilian Mafia (also known as Cosa Nostra). Dinner is on your own this evening.
After breakfast, we'll drive to 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’ll head to Segesta, a region that was home to the ancient Elymians, one of Sicily's indigenous peoples. In a reminder of Segesta's ancient Greek heritage, the columns of a beautifully preserved unfinished Doric temple still stand proudly in a majestic hilltop location. After lunch, we'll walk in the countryside to enjoy views of the surrounding olive groves, vineyards, and temple ruins. Then, we continue to Mazara, where we'll check into our hotel.
We'll gather together this evening for an included dinner at our hotel.
After breakfast, we'll embark on 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.
Then 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. Afterward we'll enjoy a traditional couscous lunch in a local restaurant.
This evening we'll learn how to prepare authentic Sicilian fare during a cooking class at a local restaurant and enjoy the food we helped to prepare during an included dinner.
Today begins with a hearty breakfast, followed by a brief visit to Museo del Sale, a semi-working salt museum where we’ll learn about the age-old Trapani tradition of salt production and refining. Then, we enjoy a boat ride (weather permitting) to the small island of Mothya. Some 2,700 years ago, the Phoenicians built a settlement here. We'll visit the ancient island fortress and enjoy a light picnic lunch amid the peaceful and historic surroundings before returning to Mazara.
This afternoon, we visit a local winery to enjoy a tasting of the renowned wines of the Marsala vineyards.
This evening, we'll enjoy dinner together at a local restaurant (Please note: Groups staying at the Berlingeri Resort will have dinner at the hotel).
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 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 enjoy 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 a bit of the town noted for the extravagant Sicilian Baroque architecture of its churches and palazzi. This evening, we'll dine like the locals and enjoy apericena, a light dinner featuring a variety of traditional Sicilian foods eaten with the fingers.
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'll make our journey to the neighboring town of Modica, part of the Val di Noto UNESCO World Heritage Site, like the Sicilian locals—aboard vintage Fiat 500s. These small, iconic Italian cars are also ideal for maneuvering through the narrow streets and lanes of Modica. 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’ll journey into the Sicilian countryside to experience A Day in the Life of a Sicilian farm. We’ll visit a farm owned by a local family and spend the day getting to know them and learning about a different side of life in rural Sicily. They will also show us some of the culinary traditions that have made Sicily famous around the world, and we'll have a chance to make bread before enjoying an authentic Sicilian lunch with our gracious hosts.
After lunch, we'll return to our hotel in Ragusa and enjoy the rest of the afternoon at leisure. 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. When we arrive, we'll set off on a discovery tour of Ortigia, where an enticing blend of architectural styles awaits, including Greek and Roman ruins, Medieval Norman structures, and Baroque buildings. Highlights include 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 lunch on your own, we'll take a boat ride along Ortigia Bay (not available November through March or in bad weather). Afterwards, 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. Then, we'll visit the local fish market, where an array of sights and sounds (and seafood!) delight. (Please note: If this day falls on a Sunday, we visit the fish market in Siracusa on Day 12 instead. Or, if this day falls on a Monday, the WWII Museum is closed and will be visited on another day.)
After lunch on your own, we'll journey to hillside Taormina, home to a Greco-Roman theater that is one of the most highly regarded ancient sites in Sicily. We'll visit this impressive amphitheater and explore the charming town, admiring its sweeping views of Mt. Etna and the Ionian Sea. This evening, we'll toast our adventure over a Farewell Drink at the hotel, followed by a Farewell 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. We'll set off on 4-wheel-drive vehicles with a local nature guide to explore some of Etna's lava caves and traces of lava flows. Please note: Today's activity may be altered due to snow or inclement weather during the winter season.
Afterward, we'll enjoy our lunch. Then we'll transfer back to Catania for time at leisure. Dinner is on your own this evening.
We depart our hotel this morning and transfer to the airport for our flight home. Or, begin our Calabria: Southern Italy's Heartland extension.
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Sprawling down rugged mountain slopes to the sea, Calabria has nourished rich cultures in dramatic settings for nearly 3,000 years. From mysterious megaliths pre-dating the Greeks to buffalo farms still making prized cheeses today, explore local gems spanning the millennia. As you hike Raganello Gorge, make local cuisine, and soak in views from the First Pearl of the Amalfi, you’ll find it easy to fall in love with Calabria.View Extension Itinerary