Overseas Adventure Travel Announcing 2026 Adventures by Land & Small Ship | Europe: Sicily's Ancient Landscapes & Timeless Traditions

EUROPE

Taormina
Taormina

Sicily: Palermo, Mazara del Vallo, Piazza Armerina, Ragusa, Catania, Mount EtnaSmall groups of no more than 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. Experience Sicily's full enchantment on a journey from the bustling markets of Palermo to the Baroque beauty of Ragusa and Catania. Hear the rumbling groans of Mount Etna, spend a night in an agriturismo, and immerse yourself in Sicily's landscapes, history, and culture.

16 days starting from $4,595
including international airfare from New York or Newark
Single Supplement: FREE
Departure Dates: Jan-Jun; Aug-Dec
Activity Level: 1 2 3 4 5 Moderate

IT'S INCLUDED

Siracusa
Siracusa
Fiat 500 ride, Modica
Fiat 500 ride, Modica

ITINERARY

DAY 1 • Depart U.S.

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

DAY 2 • Arrive in Palermo, Sicily

Arrive in Palermo and meet your fellow travelers, including those who took our Puglia: Italy's Undiscovered Heel pre-trip extension. 
Hotel Federico II or similar

DAY 3 • Palermo • Controversial Topic: The Sicilian Mafia

Explore Palermo on a walking tour. Highlights include the Piazza Pretoria, where we'll learn why its 16th-century fountain is referred to as the "Fountain of Shame," and the Teatro Massimo Vittorio Emanuele, a prominent opera house located on the Piazza Verdi. We'll also stop at the Capo Market to sample some Sicilian treats. Later, gather for an enlightening Controversial Topic about the Sicilian Mafia (also known as Cosa Nostra).
Meals: B,D | Hotel Federico II or similar

ADVENTURE HIGHLIGHT

On Day 3, learn about the Controversial Topic of the history of the Sicilian Mafia from a local expert.

DAY 4 • Palermo •  A Day in the Life of Castelbuono

Today we'll spend A Day in the Life of Castelbuono, an ancient hilltop town crowned with a medieval castle. Learn about the town's garbage-collecting donkeys, tour the castle and adjacent museum, and stroll through the Piazza Margherita. This is a great opportunity to interact with local Sicilians and see what life is really like in rural Sicily.
Meals: B,L | Hotel Federico II or similar

DAY 5 • Monreale Segesta Mazara del Vallo

Drive to Monreale and enjoy a guided visit. View the town's twelfth-century Norman Cathedral, which sits in the hills overlooking Palermo. Then, head to Segesta for an included lunch at a local agriturismo and learn about wine and olive oil production from the owner. Later, continue to Mazara del Vallo.
Meals: B,L | Mahara Hotel or similar

DAY 6 • Mazara walking tour Tunisian Kasbah Home-Hosted Lunch

Embark on a walking tour of the UNESCO-protected city of Mazara. Here, some 3,000 Tunisians and other Maghreb Arabs live and work, a mingling of cultures and faiths that has deeply influenced the city. In Mazara's historic Kasbah quarter, we'll visit a museum built to house the famous "Dancing Satyr." Later, enjoy a Home-Hosted Lunch with a local family, dining on North African-influenced Sicilian cuisine.
Meals: B,L | Mahara Hotel or similar

DAY 7 • Museo del Sale visit Mothya Island Sicilian cooking lesson

Visit Museo del Sale, a semi-working salt museum, and learn about the Trapani tradition of salt production and refinement. Then, take a boat ride (weather permitting) to the small island of Mothya. There, explore the ancient island fortress and a local museum, enjoy a picnic lunch, and take a gentle hike on one of the many foothpaths that crisscross the island.
Meals: B,L,D | Mahara Hotel or similar

DAY 8 • Overland to Piazza Armerina • Valley of the Temples • Agrigento

Depart for Piazza Armerina. En route, stop at the Valley of the Temples, situated outside the city of Agrigento, and view the archaeological remains of several Greek temples. Then, arrive at an agriturismo, our home for the night.
Meals: B,L,D | Vecchia Masseria or similar

DAY 9 • Ragusa Villa Romana del Casale • Winery tour

Depart for Villa Romana del Casale, home to the ruins of a Roman villa-a UNESCO World Heritage Site. Then, visit a family-run winery and meet the owners. Enjoy a wine tasting and lunch. Afterward, continue to Ragusa and explore the town's Sicilian Baroque churches and palazzi.
Meals: B,L,D | Hotel II Barocco or similar

DAY 10 • Old Town Ragusa Fiat ride through Modica

Explore Ragusa Ibla, one of Sicily's best-preserved old towns, and a UNESCO World Heritage Site. Then, journey to nearby Modica, part of the Val di Noto UNESCO World Heritage Site, and board vintage Fiat 500 cars to explore the city's winding streets in true Sicilian style.
Meals: B,D | Hotel II Barocco or similar

 

ADVENTURE HIGHLIGHT

On Day 10, zip through the narrow streets of Modica aboard a vintage Fiat 500.

DAY 11 • Val di Noto farm visit. Optional Marina di Ragusa tour or Optional Scicli tour

This morning, visit a family farm nestled in the Val di Noto, where you'll discover some of Sicily's renowned culinary traditions during a tour of the property and lunch with the family. This afternoon, after returning to Ragusa, you can join an optional tour to Marina di Ragusa (on May-September departures) or Scicli (on October-April departures).
Meals: B,L | Hotel Il Barocco or similar

DAY 12 • Overland to Siracusa • Ortigia Catania

After breakfast, we depart for Siracusa, 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, Siracusa boasts a rich and storied history-evident today in the city's Greek, Roman, and Baroque architecture, which has helped earn Siracusa UNESCO World Heritage Site designation. When we arrive, we'll set off on a discovery tour of Ortigia. Highlights include the fountain of Arethusa, the Temple of Apollo, and the Piazza del Duomo. Then, continue to Catania.
Meals: B,D | Hotel Una Palace or similar

DAY 13 • Catania World War II Museum • Conversation about volcanology

Explore Catania, a vibrant city perched on the edge of the lonian Sea. We'll set out to discover the city on foot, stopping along the way at the UNESCO-protected Cathedral of Catania. Originally erected in the eleventh century, it has endured damage from numerous earthquakes over the years and today features a rich blend of Norman and Baroque architecture from its many repairs. Afterwards, visit Catania's local World War II Museum, dedicated to the Allied landing on the southern coast of Sicily. Later, meet with a local volcanologist to learn about life in a volcanic region.
Meals: B,L | Hotel Una Palace or similar

DAY 14 • Catania Overland to Taormina

Visit hillside Taormina, home to a Greco-Roman theater that is one of the most highly regarded ancient sites in Sicily. Get to know the city during a walking tour. We'll visit the famous amphitheater and take in a commanding view-perched atop a hill, the brick and stone structure offers a view of the building-speckled coastline, the lonian Sea, and Mount Etna. Moving on, we'll explore Taormina's more contemporary delights: winding streets lined by pastel-hued buildings, many accented by wrought-iron balconies.
Meals: B | Hotel Una Palace or similar

DAY 15 • Catania Excursion to Mount Etna

Journey to Mount Etna, Europe's tallest active volcano, and enjoy a 4-wheel-drive experience to explore traces of Etna's lava flows before enjoying lunch. Then transfer back to Catania. This evening, enjoy a Farewell Dinner at a local restaurant.
Meals: B,L,D | Hotel Una Palace or similar

DAY 16 • Return to U.S.

Transfer to the airport for your flight home. Or, begin our Calabria: Southern Italy's Hidden Heartland or Amalfi Coast & Naples: Terraced Cliffs, Turquoise Waters & Ancient Ruins post-trip extension.
Meals: B

Agrigento
Agrigento
Fish Market, Catania
Fish Market, Catania

Want to know more? Find the full itinerary and dates & pricing at www.oattravel.com/bya

Special Departure available on this adventure. Call for details.

PERSONALIZE YOUR EXPERIENCE on your Sicily adventure

OPTIONAL EXTENSIONS

Choose to maximize your discoveries and value when you add a pre- or post-trip extension-or both-to your adventure.

Puglia: Italy's Undiscovered Heel

PRE-TRIP: 5 nights from $1,895

Alberobello
Alberobello

Witness the full range of Puglia's hidden treasures-from the Baroque beauty of Lecce to the unique conical-roofed homes of Alberobello.

IT'S INCLUDED

Learn more at www.oattravel.com/bya-puglia-2026

Calabria: Southern Italy’s Hidden Heartland

POST-TRIP: 5 nights from $1,795

Tropea
Tropea

Soak in views of hilltop villages, witness mysterious megaliths, and visit ancient stone cities in Italy's Calabria region.

IT'S INCLUDED

Learn more at www.oattravel.com/bya-calabria-2026

Amalfi Coast & Naples: Terraced Cliffs, Turquoise Waters and Ancient Ruins

POST-TRIP: 6 nights from $2,595

Amalfi
Amalfi

Experience the turquoise waters, sun-bleached villas, and precipitous cliffs of the Amalfi Coast, and witness the archaeological treasures of Naples.

IT'S INCLUDED

Learn more at www.oattravel.com/bya-amalfi-2026

ARRIVE EARLY

We recommend that you relax after a long flight or explore more in depth before your trip. Price shown includes accommodations and private airport transfer.