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2016 Sicily's Ancient Landscapes & Timeless Traditions

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Palermo • Mazara del Vallo • Piazza Armerina • Ragusa • Catania

Courtesy Emeric Livinec
Land of Sicilia

Witness some of the gorgeous Sicilian scenery; from mountaintops to craggy shorelines and charming ancient cities.

©2013 The New York Times
The Italian Gesture

See why Italians favor talking with their hands, and learn to interpert the gestures often accompanying conversation.

Courtesy Dmitry Khudyakov
Sicily Timelapse

Witness the simple beauty of Sicily from above as you pass beloved landmarks and hillside towns.

Courtesy Silvia Santamaria and Ian Cross
Bazaar: Sicily

Delve into eastern Sicily’s cultural gems, from wine produced on Mount Etna to elaborate puppets and colorful ceramics.

Courtesy Giuseppe Vetrano
Echoes from the Middle Ages

Travel back to antiquity when you explore Erice’s ancient stone town with sweeping views of Sicily.

Trip Experience

Meet three friendly locals who make Sicily such an inviting destination.

Trip Itinerary

Watch a detailed overview of the unique history and cultural riches you’ll uncover on this adventure.

Trip Leader

Tune in to hear Trip Leader Isabella Trovato discuss what it's like to hike on Mount Etna and why she volunteers at an animal shelter.

Trip Leader

Meet Trip Leader Giuseppe Lenzo who harvests olives with his family and knows the secret behind the recipe for caponata.

Trip Extension: Puglia

Meet friendly locals and find out how olive oil is a way of life on a trip extension to Puglia.

Trip Extension: Calabria

Interact with a sculptor and a charming town mayor on this trip's extension to Calabria.

Trip Preview

Take a peek at the adventures that await you in Sicily, from roaming through lush vineyards to riding a donkey on Mount Etna.

Courtesy Lawrence Edward Clift
Teatro Greco, Taormina, Sicily

Enjoy a panoramic glance above the Greco-Roman theater of Taormina, Sicily, and its surrounding environs.

Courtesy Small World Productions

Join travel expert Rudy Maxa for a tour of Sicily’s timeless treasures.

Courtesy Small World Productions

Discover southern Italy’s exuberant culture and the stunning beauty of the Amalfi Coast with travel expert Rudy Maxa.

New Year, New Stories

Take a look at the films that inspire filmmaker David Conover—and preview the stories that await this year.

Climate Change & Travel

Travel with David Conover to see how people—from street protesters to Heads of State—respond to a changing climate and ocean.

Produced for CuriosityStream
Big Picture Earth Trailer

David Conover's newest television series takes us from Stonehenge to Petra, from Iceland to the Oracle at Delphi ... and beyond.

Sharing Travel Moments

Hear why visual storytelling helps to build a conversation about the world from filmmaker David Conover.

Solo Traveler Experience

Meet a solo traveler who shares her reasons for exploring the world with Overseas Adventure Travel.

The O.A.T. Experience

See what you can expect when you travel in your small group on the road less traveled with O.A.T.

Travel Protection Plan

Learn about the benefits of O.A.T.'s plan—and how you can protect your entire trip investment.

Sold out in 2016 , Join us in 2017
Extend Your Trip

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Itinerary Overview

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.

Day-to-Day Itinerary

  • 5 nights from only $1395

    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
Palermo Catania Expand All
  • 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, followed by a brief Italian lesson while meeting with 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.

  • 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 one of the city's historic quarters, with a walk through a traditional market to enjoy a lunch featuring the local street food—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. Later, our group will gather for an enlightening discussion about the Sicilian Mafia (also known as Cosa Nostra), followed by dinner on your own tonight.

  • 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. Dinner is on your own this evening.

  • After breakfast, we'll drive to Erice, a wonderfully preserved medieval town that towers over Sicily's western coast. After a walking tour of the ancient mountain-top town, we’ll head to Segesta, a region that was home to the ancient Elymians, one of Sicily's indigenous peoples. 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. Later, we’ll enjoy 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 during an enlightening discussion with some Tunisian locals. Afterward we'll enjoy a traditional couscous lunch in the heart of the Kasbah.

    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 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 first enjoy 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 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.

  • 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 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 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. 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 to the village of Castelluccio, where we’ll experience A Day in the Life of a Sicilian dairy farm. We’ll visit a dairy farm owned by a local family, who will be happy to show us some of the culinary traditions that have made Sicily famous around the world. We’ll begin by seeing how they make cheese, specifically ricotta, which, in Italy, is typically made from sheep’s milk (while in the U.S., it’s usually made with cow’s milk). Cheese experts often say that the difference between fresh ricotta and store-bought ricotta is stark—and we’ll be able to test this theory for ourselves as we sample the fruit of our labor.  We’ll also have a chance to bake bread before enjoying an authentic Sicilian lunch with our 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. Our tour concludes with a stroll along Via Crociferi, a scenic passage laced with churches, monasteries, and private homes.

    After lunch on your own, we'll journey to hillside Taormina, one of the most highly regarded ruins in Sicily. We'll tour the ancient site with its impressive Greek amphitheater, as well as the charming village of Taormina, and admire sweeping views of Mt. Etna and the Ionian Sea.

    Dinner is on your own this evening.

  • 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 journey up to Piano Provenzana, a former ski station at an altitude of almost 6,000 feet. Then, we'll have an opportunity to trek a little by donkey (and also by foot) to admire the surrounding mountain views. Please note: Departures from November-March will not visit Piano Provenzana, but will enjoy these activities from Linguaglossa.

    Afterward, we'll enjoy a barbecue lunch. 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.

    • Meals included:

    We depart our hotel this morning and transfer to the airport for our flight home. Or, begin our Calabria: Southern Italy's Heartland extension.

    Calabria: Southern Italy’s Heartland

    7 nights from only $1695

    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

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