Print

Day by Day Itinerary

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.

Palermo Catania Expand All
  • hidden

    Fly overnight from the U.S. to Palermo, Sicily.

  • hidden

    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.

  • hidden

    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 most ancient areas of the city, 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. Later, our group will gather for an enlightening discussion about the Sicilian Mafia (also known as Cosa Nostra) with one of the sons of a former Mafia boss, followed by dinner on your own tonight.

  • hidden

    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.

    Dinner is on your own this evening.

  • hidden

    After breakfast, we depart for Mazara del Vallo, one of Italy’s premier deep-sea fishing ports. En route, we stop in the ancient fishing village of Scopello, home to an old tuna fishery (Tonarra) and dramatic rock towers where scenes from the film Ocean's Twelve were filmed. Then, we'll enjoy a hike in the nearby Zingaro Nature Reserve, a scenic region where the sea has sculpted many coves and grottoes into the limestone cliffs. If weather permits, we'll also take a boat ride across the bay to the coastal town of San Vito Lo Capo, where we disembark for lunch at a local restaurant.

    Later this afternoon, we continue to Mazara, where we’ll check into our hotel and enjoy dinner together this evening.

  • hidden

    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.

  • hidden

    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.

    Later 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 enjoy a traditional couscous dinner in the heart of the Kasbah.

  • hidden

    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.

  • hidden

    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.

  • hidden

    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.

  • hidden

    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. We'll enjoy some hiking in this marshland oasis that is temporary home to thousands of migratory birds heading to or from Africa. Lunch is on your own.

    After returning to Ragusa, dinner is on your own this evening.

  • hidden

    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.

  • hidden

    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.

  • hidden

    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.

  • hidden

    • 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.

Extensions

Traveler Reviews

There's no better way to learn what a trip is like than from the firsthand experiences of your fellow travelers, and our Traveler Reviews are the real deal—unbiased and unedited—giving you an honest appraisal of the experiences that await you on this trip.

Have you been on this trip? Share Your Thoughts, Sign In

Please note: If you have taken this trip, please log into your My Account & return to this page. You will be prompted to post your review. Reviews are limited to 10,000 characters. Due to our moderation process, please allow up to 72 hours for your review to appear.

loading reviews

Weather & Regional

Before you travel, we encourage you to learn about the region of the world you'll discover on this trip. From weather and currency information to details on population, geography, and local history, you'll find a comprehensive introduction to your destinations below.  Visit our “What to Know” page to find information about the level of activity to expect, vaccination information resources, and visa requirements specific to this vacation.

What to Know

For more detailed information about this trip, download our Travel Handbook below. This document covers a wide range of information on specific areas of your trip, from passport, visa, and medical requirements; to the currencies of the countries you’ll visit and the types of electrical outlets you’ll encounter. This handbook is written expressly for this itinerary. For your convenience, we've highlighted our travelers' most common areas of interest on this page.

Download the Travel Handbook

What to Expect

Pacing

  • 5 locations in 14 days with one 2-night stays
  • International flights to Sicily depart around midnight
  • Airport transfers in Palermo and Catania can take more than 30 minutes

Physical Requirements

  • Not appropriate for travelers using wheelchairs, walkers, or other mobility aids
  • You must be able to walk 3 miles unassisted and participate in 6 hours of physical activities each day
  • Agility and balance are required for embarking small boat and for donkey ride

Climate

  • Daytime temperatures range from 60-95°F
  • Sicily has a typical Mediterranean climate, with hot, dry summers and warm, rainy winters

Terrain

  • Travel on some rugged paths and many cobblestoned streets on foot, as well as over bumpy, narrow rural roads by bus

Transportation

  • Travel by 30-passenger coach, 20-40-passenger boat, and donkey
  • 4-hour drives

Accommodations & Facilities

  • Hotel rooms are smaller than U.S. and offer basic amenities
  • All accommodations feature private baths

Travel Documents

Passport

Your passport should meet these requirements for this itinerary:

  • It should be valid for at least 6 months after your scheduled return to the U.S.
  • It should have the recommended number of blank pages (refer to the handbook for details).
  • The blank pages must be labeled “Visas” at the top. Pages labeled “Amendments and Endorsements” are not acceptable.

Visas

U.S. citizens do not need a visa for this trip.

If you are not a U.S. citizen, do not travel with a U.S. passport, or will be traveling independently before/after this trip, then you may need a visa. Please check with the appropriate embassy or a visa servicing company. To contact our recommended visa servicing company, PVS International, call toll-free at 1-800-556-9990.

Vaccinations Information

For a detailed and up-to-date list of vaccinations that are recommended for this trip, please visit the CDC’s “Traveler’s Health” website. You can also refer to the handbook for details.

Before Your Trip

Before you leave on your adventure, there are at least four health-related things you should do. Please check the handbook for specifics, but for now, here’s the short list:

Step 1: Check with the CDC for their recommendations for the countries you’ll be visiting.
Step 2: Have a medical checkup with your doctor.
Step 3: Pick up any necessary medications, both prescription and over-the-counter.
Step 4: Have a dental and/or eye checkup. (Recommended, but less important than steps 1-3.)

What to Bring

In an effort to help you bring less, we have included checklists within the handbook, which have been compiled from suggestions by Trip Leaders and former travelers. The lists are only jumping-off points—they offer recommendations based on experience, but not requirements. You might also want to refer to the climate charts in the handbook or online weather forecasts before you pack. Refer to the handbook for details.

Insider Tips

Accommodations

Main Trip

  • Hotel Plaza Opera

    Palermo, Italy

    Situated near the Piazza Politeama in the heart of Palermo, the Hotel Plaza Opera includes a bar/lounge and rooftop terrace. There are 47 air-conditioned, contemporary styled rooms, each with parquet wood floors, minibar, safe, satellite TV, and private bath with hair dryer.

  • Visir Resort & Spa

    Mazara del Vallo, Italy

    Located outside the bustle of the city center, this resort-style hotel features an outdoor and indoor pool, as well as a full-service spa. Each of the 27 air-conditioned, soundproof rooms feature a private bath with hair dryer and bathrobes. Guests can enjoy the Arab and Mediterranean decor as they relax at the on-site café, lounge, and poolside bar.

  • Gigliotto Agriturism

    Piazza Armerina, Italy

    Located at the site of a 13th-century monastery, this property is now a charming and intimate farmhouse that welcomes guests from around the world. Gigliotto Agriturism is situated on a 740-acre estate, and has 14 comfortable rooms (each with private bath) as well as a swimming pool with a sun deck. The property also has its own organic farm and vineyard, and full-service restaurant.

  • De Stefano Palace

    Ragusa, Italy

    De Stefano Palace is situated in Situated in the heart of historic Ragusa, near Palazzo Bertini and the Church of Santa Maria dell'Itria. Hotel amenities include a bar and lounge and complimentary wireless Internet. There are 14 air-conditioned rooms, each with minibar, safe, satellite TV, and private bath with hair dryer.

  • Katane Palace Hotel

    Catania, Italy

    Set in the heart of Catania, the Katane is just a few minutes’ drive away from Corso Italia and the Duomo cathedral. The 58 air-conditioned rooms each have a minibar, hair dryer, safe, satellite TV, private bath, and city or garden views. Enjoy excellent wines at the bar and superb Sicilian fare at the Il Cuciniere restaurant.

Extensions

  • Locanda di San Martino

    Matera, Italy

    The Locanda di San Martino Hotel is situated in the heart of Matera, close to the cathedral and the ancient dwellings of Sassi. Facilities include a bar/lounge, indoor pool, spa, and fitness center. There are 32 air-conditioned rooms at the hotel, each with minibar, satellite TV, complimentary wireless Internet, and private bath with hair dryer.

  • Villa Velia

    Monterosso, Italy

    Built to resemble an ancient Roman villa, the Villa Velia is an agriturismo farmhouse situated on a high ridge overlooking the Angitola Valley. Amenities include a restaurant and a tasting room, both featuring specialties of the region and produce grown on the farm. Rooms are simple and all include private bath (with no TV or telephone).

  • B & B La Ginestra

    Civita, Italy

    La Ginestra is one of several Bed & Breakfast-style accommodations situated in ancient Civita on the slopes of Mount Pollino. Rooms at La Ginestra have air-conditioning, satellite TV, coffee- and tea-making facilities, and private bath.

  • Lloyd’s Baia Hotel

    Vietri sul Mare, Italy

    Set on a private beach in the heart of Vietri sul Mare, Lloyd’s Baia Hotel features two restaurants, terrace, and bar/lounge. There are 131 rooms, each with air-conditioning, complimentary wireless Internet, TV, and private bath

Flight Information

Flight Options to Personalize Your Trip

You can choose to stay longer before or after your trip on your own, or combine two adventures to maximize your value. Here are more ways to create the OAT adventure that’s right for you:

  • Extend your adventure and lower your per day cost with our optional pre- and post-trip extensions
  • Choose our standard air routing, or work with us to select the airline and routing you prefer
  • Make your own international flight arrangements directly with the airline, applying frequent flyer miles if available
  • International airport transfers to and from your hotel, including meet and greet service, are available for purchase
  • Stay overnight in a connecting city before or after your trip
  • Request to arrive a few days early to get a fresh start on your adventure
  • Choose to “break away” before or after your trip, spending additional days or weeks on your own
  • Combine your choice of OAT adventures to maximize your value
  • Upgrade to business or premium economy class
  • Extend your Land Tour-only Travel Protection Plan coverage and protect the air arrangements you make on your own—including your frequent traveler miles

The air options listed above will involve an additional fee of $100 per person for confirmed requests (as well as incremental airfare costs based on your specific choice).

Or, when you make your reservation, you can choose our standard air routing, for which approximate travel times are shown below.

Standard Air Routing

w/out standard air $2795
w/ standard air $3995
Gateway Travel Time*
Boston, New York (JFK) 12hrs
Chicago, Detroit 13hrs
Atlanta, Houston, Miami 14hrs
Denver, Washington, DC (Dulles) 15hrs
Minneapolis, San Francisco, Seattle 16hrs
Los Angeles, Tampa 17hrs
Portland, OR 18hrs
Phoenix 19hrs
San Diego 20hrs

* Estimated total time, including connection and layover. Actual travel time may vary.

The information above reflects approximate flight times from the gateway cities listed to Palermo, Italy. Routing is based on availability and subject to change. You will receive your final air itinerary approximately 14 days prior to departure.

Sicily: The Soul of Italy

The rise of a unique culture just off the Italian mainland

by Amanda Read

If Venice and Rome are exquisitely adorned divas, Sicily is the guilelessly gorgeous girl next door, unaware of her charms.

‘To have seen Italy without having seen Sicily is to not have seen Italy at all, for in Sicily lies the key to everything.’ —Johann Wolfgang von Goethe, Italian Journey

Perhaps Goethe was a bit overzealous when he called Sicily the “key to everything” (or maybe he had enjoyed a bit too much Sicilian wine), but he was certainly on to something. Sicily’s natural beauty, culture, and history are outstanding. But Sicily’s doors don’t necessarily swing open to its visitors as easily as its more well-known Italian neighbors to the north. Like a cautious gambler, the island won’t normally reveal its hand easily. If Venice and Rome are like exquisitely made up divas, then Sicily is the naturally gorgeous girl next door who is blissfully unaware of her charms. Those who dare to unlock Sicily’s mysteries will find an authentic, Old-World Italian island full of life and character—a true diamond in the rough.

Situated in the heart of the Mediterranean Sea, Sicily lies at the tip of the “boot” of the Italian peninsula. Thanks to its fertile volcanic soils and its advantageous position at the crossroads of Europe’s oldest trade routes, Sicily became a desirable catch for endless invaders and occupiers. Everyone wanted her, and the island became the playground for numerous cultures.

A tumultuous past

The Greeks were the first to be attracted to Sicily’s shores almost 3,000 years ago. Romans, Carthaginians, Byzantines, Arabs, Normans, and Spaniards followed—just to name a few. Each of these peoples left their unique mark on Sicily, before being pushed out by the next wave of intruders, resulting in one of the most captivating cultural mélanges in the world. Where else can one see ancient Greek temples, Roman amphitheaters, Norman fortresses, and Baroque cathedrals all in one place?

While the cultural treasures left behind by Sicily’s numerous conquerors were certainly a blessing, almost 3,000 years of foreign domination also took its toll on the island. Plundered and subjugated by so many different powers, Sicily ended up a rather poor and impoverished region. Having been exploited for so long, Sicilians built up a strong sense of kinship among themselves while trying to survive in a cruel world, as well as a deep-rooted mistrust of all sorts of government authority. This is originally how the mafia gained a toehold here. Formed as a secret organization to fight against the rulers who had crushed the country and its people for centuries, it later became something more sinister.

Sicily is different

Locals think of themselves as Sicilian first and Italian second; when Sicilians visit the Italian mainland, they are off to “Il Continente.” Although the Strait of Messina separating Sicily from the rest of Italy is only 2.5 miles wide, the cultural gap couldn’t be greater. Sicily seems a world apart.

And speaking about differences: not only does the Sicilian dialect sound distinctly different than those of other parts of Italy, the cuisine here differs even more. The food alone makes a trip here worthwhile. One could consider it the original fusion cuisine—a blend of ingredients from Arab, North African, Greek, Italian, and Spanish traditions to create exquisite and exotic dishes. This diversity makes the Sicilian kitchen the most versatile in the Mediterranean.

Sicily’s rich culinary tradition dates back to when the first Greek colonists arrived here in the eighth century BC. In fact, the very first cookbook in Europe was written in Sicily by the ancient Greek chef Mithoecus. And one of Sicily’s classics, Spaghetti con le Sarde—pasta with sardines, pine nuts, wild fennel, and raisins—is thought to date back to the Arab’s first expedition into Sicily in the year AD 827. The story goes that the army cooks were ordered to forage for food and found sardines at the port, wild fennel from the fields, and raisins drying in the vineyards. Somehow the combination worked.

Perhaps the thing that most distinguishes Sicily from the rest of the country, though, is its people and their unique way of living. Those who enjoy Italy for its warm-hearted people and their joy of life (la dolce vita) will never forget the intensity of the Sicilian experience. It is here where they have truly mastered the sweet art of doing nothing (dolce far niente). Sicily is still authentic, Old World Italy at its best.