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The Leader in Small Groups on the Road Less Traveled
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2018 Sicily's Ancient Landscapes & Timeless Traditions

Sicily: Palermo, Mazara del Vallo, Piazza Armerina, Ragusa, Catania

90% Traveler Excellence Rating Read reviews

15 Days from only $3595 including international airfare

View details

Activity Level:

1 2 3 4 5


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 Emeric Livinec
Land of Sicilia

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

Courtesy of Epicurious
How to Make Italian Pasta Bolognese

Let chef Joseph DiPerri guide you through preparing traditional pasta Bolognese in this short film.

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.

including international airfare
14 DAYS FROM $2495 Small Group Adventure Only
Extend Your Trip

Save $500 on airfare to Sicily
on January-June 2018 departures
Reserve by 10/6/17 >>


This trip features long flights and/or multiple connections.
Learn More »

For example, combine this trip with Tuscany & Umbria.
See More Options »

Find the Adventure That’s Right for You

Our Activity Level rating system ranks adventures on a scale of 1 to 5 to help you determine if a trip is right for you. See the descriptions below for more information about the physical requirements associated with each rating.

Activity Level 1:

1 2 3 4 5


Travelers should be able to climb 25 stairs consecutively, plus walk at least 1-2 miles over some uneven surfaces without difficulty. Walks typically last at least 1-2 hours at a time. Altitude can range from zero to 5,000 feet.

Activity Level 2:

1 2 3 4 5

Moderately Easy

Travelers should be able to climb 40 stairs consecutively, plus walk at least 2-3 miles over some uneven surfaces without difficulty. Walks typically last for at least 2-3 hours at a time. Altitude can range from zero to 5,000 feet.

Activity Level 3:

1 2 3 4 5


Travelers should be able to climb 60 stairs consecutively, plus walk at least 3 miles over some steep slopes and loose or uneven surfaces without difficulty. Walks typically last for 3 or more hours at a time. Altitude can range from 5,000 to 7,000 feet.

Activity Level 4:

1 2 3 4 5

Moderately Strenuous

Travelers should be able to climb 80 stairs consecutively, plus walk at least 4 miles over some steep slopes and loose or uneven surfaces without difficulty. Walks typically last for 4 or more hours at a time. Altitude can range from 7,000 to 9,000 feet.

Activity Level 5:

1 2 3 4 5


Travelers should be able to climb 100 or more stairs consecutively, plus walk at least 8 miles over some steep slopes and loose or uneven surfaces without difficulty. Walks typically last for 4 or more hours at a time. Altitude can range from 10,000 feet or more.

Itinerary Overview

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 Mount. 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.

Make It Your Adventure

Personalize your trip to meet your individual needs, from preferred flights and air routing, to “breaking away” to spend more time in a destination.

  • Did you know that you have control over the way you want to fly with us? O.A.T’s team of Adventure Specialists makes every effort to provide you with non-stop flights and acceptable connection times to and from your destination. You also have several other ways you can personalize your air itinerary, which include:

    • Choose your departure city and airline: We list the most popular gateway cities on our website, but not all of them. If you don’t see yours listed, or there’s one that better suits your needs, let us know. You can also tell us if you have an airline preference and we will try to accommodation your request.
    • Depart from one city and return from another: Just because your flight leaves from one city doesn’t mean you have to return there. Maybe you flew out of Boston and wish to visit friends in Los Angeles after your trip is over. Tell us where you want to go and we’ll do our best to get you there.
    • Upgrade your seat: We’ll gladly arrange a flight upgrade to business or premium economy class if it’s available. 
    • Fly the way you want to: When you fly economy class, we’ll do our best to see that you get your choice of seating preference or even add a special meal request if you have dietary restrictions or needs.
  • You can extend your time abroad and "break away" anywhere you'd like to do more exploring on your own. Stay for a day, a week, or even a month in a favorite locale. Or consider arriving a few days early in Palermo for a fresh start or staying overnight in a connecting city such as RomeAmsterdam, or Munich before or after your adventure to break up a lengthy flight. Our Adventure Specialists can provide you with information on the accommodations we will use at the beginning of your trip so that you can make your own arrangements. That way, you'll know that you will be exactly where you need to be to meet your group.

  • Many of our travelers choose to take another trip directly after their first one ends. Think about it: If you’re already overseas, why not see more of the region and avoid the expense and length of another international flight? Many of our travelers have taken two or three consecutive trips before returning home. One of the most common adventures combined with Sicily's Ancient Landscapes & Timeless Traditions is Tuscany & Umbria: Rustic Beauty in the Italian Heartland. And now you’ll save an additional $250-$350 per person when you reserve two trips right after one another.

  • Many O.A.T. travelers simply don’t want their trips to end. With an array of pre- and post-trip extensions to choose from, you have the chance to experience more of the places you’ve traveled so far to see, including Puglia: Italy's Undiscovered Heel and Calabria: Southern Italy’s Heartland. Plus, you lower your average per-day costs because you’re taking advantage of your already included international airfare.

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 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.

    • Meals included:
    • Accommodations:

    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 the area of 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.

    • Meals included:
    • Accommodations:

    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 and 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.

    • Meals included:
    • Accommodations:

    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. We'll 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 insteadOr, 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.

    • 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

    5 nights from only $1445

    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

Click below to read our Travel Planning Guide on Sicily's Ancient Landscapes & Timeless Traditions

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