EUROPE
Sicily: Taormina, Aeolian Islands | Italy: Reggio Calabria, Cosenza, Alberobello, Trani
Small groups of no more than 16 travelers, guaranteed
Seek out the undiscovered gems of southern Italy on a journey through Sicily, the Aeolian Islands, Calabria, Puglia, and beyond. You'll discover ancient ruins set against mountain backdrops, small medieval villages blooming with wildflowers, and the natural wonders of Italy. Castles, cathedrals, quaint harbors, and olive groves are all waiting for you on this adventure through the lesser-visited regions of Sicily and southern Italy.
18 days starting from $6,795
including international airfare from New York
Single Supplement: FREE
Departure Dates: Mar-Jun; Sep-Nov
Activity Level: Moderate
IT'S INCLUDED
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16 nights accommodation
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International airfare, airport transfers, government taxes, fees, and airline fuel surcharges unless you choose to make your own air arrangements
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All land transportation
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33 meals-16 breakfasts, 11 lunches, and 6 dinners (including 1 Home-Hosted Lunch)
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24 small group activities
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Services of a local O.A.T. Trip Experience Leader
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Gratuities for local guides, drivers, and luggage porters
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5% Frequent Traveler Credit toward your next adventure
ITINERARY
DAY 1 • Depart U.S.
Fly to Catania, Italy.
DAY 2 • Catania, Sicily • Transfer to Taormina
Arrive in Catania, where we'll meet our Trip Experience Leader and fellow travelers, including those who took The Maltese Archipelago pre-trip extension.
Excelsior Palace Hotel or similar
DAY 3 • Taormina • Greco-Roman Amphitheater
Explore Taormina during a walking tour, including the Greco-Roman amphitheater. Tonight, enjoy a Welcome Dinner at a local restaurant.
Meals: B,D | Excelsior Palace Hotel or similar
DAY 4 • Taormina • Savoca • The Godfather tour • Controversial Topic: The Sicilian Mafia • Home-Hosted Lunch
Step into the setting of Francis Ford Coppola's The Godfather as you visit a few of the film's Sicilian locations. Then, enjoy a Controversial Topic discussion on the Sicilian Mafia and a Home-Hosted Lunch with a rural Sicilian family.
Meals: B,L | Excelsior Palace Hotel or similar
DAY 5 • Taormina • Ferry to Aeolian Islands • Lipari
Take a ferry from mainland Sicily to Lipari, the largest and most populated of the Aeolian islands.
Meals: B,L | Arciduca Grand Hotel or similar
DAY 6 • Explore Lipari
Explore Lipari on a walking tour. Highlights include Corso Vittorio Emanuele, the Marina Corta town square, and the Archaeological Museum.
Meals: B,D | Arciduca Grand Hotel or similar
DAY 7 • Lipari • Salina • A Day in the Life of an Aeolian Island farm
Take a ferry to another Aeolian island, Salina, for A Day in the Life experience, where you'll spend time on a farmstead and enjoy a farm-fresh lunch.
Meals: B,L | Arciduca Grand Hotel or similar
ADVENTURE HIGHLIGHT
On Day 7, spend A Day in the Life of a farm in the Aeolian islands.
DAY 8 • Lipari • Ferry to Reggio Calabria • Scilla
Transfer to Reggio Calabria on Italy's mainland via ferry. We'll explore the nearby ancient town of Scilla, known for its cliffside castle and pristine beach, before settling in to our hotel.
Meals: B,L,D | Hotel Medinblu or similar
DAY 9 • Reggio Calabria • Museo Archeologico Nazionale • Optional Pentedattilo tour
Explore Reggio Calabria today on a walking tour with a local guide, ending in the Museo Archeologico Nazionale. Later, choose to take an optional tour to the ancient village of Pentedattilo, where we'll visit with local artisans and peruse their handmade wares, as well as hike to the "five fingers" cliffs.
Meals: B | Hotel Medinblu or similar
DAY 10 • Reggio Calabria • Explore Gerace
Delve into Gerace, a picturesque village perched atop a rock fortification, with a local guide.
Meals: B,L | Hotel Medinblu or similar
DAY 11 • Reggio Calabria • Pizzo • Cosenza
Depart for Cosenza, an ancient city in the heart of Italy's Calabria region. We'll stop along the way in the historic seaport of Pizzo for a walking tour.
Meals: B,D | Royal Hotel or similar
DAY 12 • Discover Morano Calabro & Nibbio Museum • Overland to Alberobello
Discover the hillside town of Morano Calabro on a walking tour with a local guide, including a visit to the Nibbio Museum, for an in-depth introduction to the region's fascinating plant and animal life. Later, arrive at your hotel in Alberobello.
Meals: B,L,D | Grand Hotel Olimpo or similar
DAY 13 • Explore Alberobello • Visit a local cheese farm
Discover Alberobello, a UNESCO World Heritage Site known for its iconic conical-roofed homes, or trulli. Afterward, depart for a local cheese farm, where we'll enjoy lunch.
Meals: B,L | Grand Hotel Olimpo or similar
DAY 14 • Discover Locorotondo • Visit a local capicolli farm • Optional tour to the grottos of Monopoli
This morning, we'll visit Locelobello, a whitewashed town known for its unique circular layout. Then, we'll drive to a local farm that specializes in the production of capicolli, or dry-cured pork, including a tasting over lunch. This afternoon, join an optional tour to the grottos of Monopoli.
Meals: B,L | Grand Hotel Olimpo or similar
DAY 15 • Explore Matera • Transfer to Trani
A local guide will show you around the UNESCO World Heritage city of Matera. Later, continue on to the seaport city of Trani.
Meals: B,L,D | San Paolo al Convento or similar
ADVENTURE HIGHLIGHT
On Day 15, explore the cave churches and crypts of Matera—a UNESCO World Heritage Site.
DAY 16 • Explore Trani • Visit a wine and olive oil farm
We'll embark on a guided tour of Trani. Afterward, visit a local wine and olive oil farm to learn about these important agricultural products.
Meals: B,L | San Paolo al Convento or similar
DAY 17 • Trani • Visit Castel del Monte
We'll begin today with a tour of Castel del Monte, a 13th-century citadel and castle. Later, we'll enjoy a festive Farewell Dinner at a local restaurant.
Meals: B,D | San Paolo al Convento or similar
DAY 18 • Return to U.S.
Fly to the U.S., or begin your The Amalfi Coast & Sorrento post-trip extension.
Meals: B
Want to know more? Find the full itinerary and dates & pricing at www.oattravel.com/sim
PERSONALIZE YOUR EXPERIENCE on your Sicily & Southern Italy adventure
OPTIONAL EXTENSIONS
Choose to maximize your discoveries and value when you add a pre- or post-trip extension-or both-to your adventure.
The Maltese Archipelago
PRE-TRIP: 5 nights from $2,195
Journey to the Maltese Islands, where you'll be welcomed by a warm, friendly people and bask in their sun-kissed Mediterranean climate as you share the rich heritage of their country.
IT'S INCLUDED
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Airfare from Valletta to Catania
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5 nights accommodation
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8 meals—5 breakfasts, 2 lunches, and 1 dinner
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7 small group activities
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Services of a local O.A.T. Trip Experience Leader
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Gratuities for local guides, drivers, and luggage porters
- All transfers
Learn more at www.oattravel.com/sim-malta-2026
The Amalfi Coast & Sorrento
POST-TRIP: 6 nights from $2,795
Explore the legendary and captivating Amalfi Coast, where turquoise Tyrrhenian waters, sun-bleached villas, and precipitous cliffs make up the stunning vistas.
IT'S INCLUDED
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Overland transfer to Amalfi
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6 nights accommodation
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12 meals—6 breakfasts, 3 lunch, and 3 dinners
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7 small group activities
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Services of a local O.A.T. Trip Experience Leader
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Gratuities for local guides, drivers, and luggage porters
- All transfers
Learn more at www.oattravel.com/sim-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.
- Arrive early in Valletta before your Malta pre-trip extension from $280 per room, per night
- Arrive early in Taormina before your main adventure from $320 per room, per night