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Sicily: A Cultural...

Sicily: A Cultural Journey

12 days |  14 days with Taormina Region extension
12 days |  14 days with Taormina Region extension
Group size1538 travelers

4.7 out of 5 stars

Physical activity
OverviewItineraryDates & pricesReviewsTraveler photosHotels, flights & FAQ
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The Sicilian sun shines light on a different side of Italy.

In the midst of the Mediterranean, discover an island with personality all its own—full of flavor and teeming with one-of-a-kind art and architecture. From multicultural Palermo to breathtaking Taormina, each stop on this tour of Sicily reveals unexpected treasures.

Your tour package includes

  • 10 nights in handpicked hotels
  • 10 breakfasts
  • 4 dinners with beer or wine
  • 1 wine tasting
  • 1 food tasting
Read more

Included highlights

  • Cappella Palatina
  • Monreale Cathedral
  • Agrigento's Greek ruins
  • Piazza Armerina
  • Syracuse Cathedral
Read more
Start planning today

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Day-by-day itinerary

Print itinerary
Overnight Flight1 night
Day 1: Travel day

Board your overnight flight to Palermo today.

Palermo3 nights
Day 2: Arrival in Palermo
Included meal: Welcome dinner

Welcome to Italy! Meet your Tour Director and fellow travelers at tonight’s welcome dinner.

Day 3: Sightseeing tour of Palermo & Monreale
Included meal: Breakfast

This morning, embark on a guided tour of the bayside city of Palermo and the hilltop town of Monreale.

  • Discover the city’s Baroque architecture as you pass the Quattro Canti piazza in the historic center.
  • Step inside the Cappella Palatina to see the stunning mosaics and artwork.
  • Head to nearby Monreale and enter Monreale Cathedral, a UNESCO World Heritage site that combines Norman, Arab, and Byzantine architectural styles.
Day 4: Free day in Palermo
Included meal: Breakfast

Enjoy a free day in Palermo or add an excursion.

Ancient Ruins: Segesta & Erice

From $119 per person

Enna Region1 night
Day 5: Enna Region via Agrigento
Included meals: Breakfast, Dinner

Travel south through the Sicilian countryside to Agrigento for a guided walking tour of the city’s fascinating Greek ruins.

Continue on to the Enna region and sit down for an included dinner.

Syracuse4 nights
Day 6: Syracuse via Piazza Armerina
Included meals: Breakfast, Dinner

On the way to Syracuse, stop for a guided tour of Piazza Armerina and view the stunning mosaics in Villa Romana del Casale, a UNESCO World Heritage site.

Sit down for an included dinner this evening.

Day 7: Sightseeing tour of Syracuse
Included meal: Breakfast

Embark on a guided tour of Syracuse, a historic city known for its rich Greek history.

  • Visit the Greek theater, the most complete ancient Greek theater still in existence.
  • Tour the massive Paradise Quarry and gardens, featuring the cave that Caravaggio dubbed “The Ear of Dionysius” for its unique acoustics.
  • Visit the Roman amphitheater, then cross a bridge to the Island of Ortygia to see the Temple of Apollo and Syracuse Cathedral.
Day 8: Free day in Syracuse
Included meal: Breakfast

Enjoy a free day in Syracuse or add an excursion.

Traditions of Sicily: Villa Lunch & Noto Village

From $125 per person

Day 9: Modica & sightseeing tour of Ragusa
Included meals: Breakfast, Tasting, Wine tasting

Head out into the Sicilian countryside today.

  • Make a stop in the city of Modica for a tasting at the oldest chocolate shop in Sicily.
  • Head to the hilltop town of Ragusa for a tour with a local guide.
  • Stroll through Ragusa Ibla, the UNESCO-protected old town, past Baroque-style palaces and churches.
  • Step inside a local shop for a tasting of Cerasuolo di Vittoria wine.
Taormina Region2 nights
Day 10: Transfer to Taormina & sightseeing tour
Included meal: Breakfast

Transfer to Taormina, where a local guide introduces you to this scenic town perched high above the sea.

  • Enjoy views of Mount Etna, Taormina Cathedral, and Palazzo Corvaja, seat of the first Sicilian parliament.
  • Visit the town’s 2nd-century Greek theater.

Enjoy a free evening in the Taormina region or add an excursion.

Traditional Sicilian Dinner & Wine Tasting

From $109 per person

Day 11: Free day in the Taormina Region
Included meals: Breakfast, Farewell dinner

Enjoy a free day in the Taormina region or add an excursion.

This evening, celebrate your trip with your group during a farewell dinner.

Mount Etna: Sicily's Volcanic Landscapes

From $95 per person

Flight Home
Day 12: Departure
Included meal: Breakfast (excluding early morning departures)

Transfer to the Catania airport for your flight home or extend your stay in Taormina.

Extension to Taormina Region
“Picturesque” is the word that springs to mind when we think of the Taormina region’s pretty piazzas and ocean vistas (although “jaw-dropping” and “mesmerizing” work, too). Extend your stay in Sicily to soak in more of this lovely locale with your Tour Director by your side.
Taormina Region2 nights
Day 12: Free day in the Taormina Region
Included meal: Breakfast

Enjoy a free day in the Taormina region or add an excursion.

Hidden Sicily: Medieval Savoca & Forza d’Agrò

From $65 per person

Day 13: Free day in the Taormina Region
Included meal: Breakfast

Spend a free day in the Taormina region or add an excursion.

This evening, enjoy a farewell drink as you celebrate your trip with your fellow group members.

Museo Storico dello Sbarco & Historic Catania

From $65 per person

Flight Home
Day 14: Departure
Included meal: Breakfast (excluding early morning departures)

Transfer to the Catania airport for your flight home.

Show full itinerary
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4.7 out of 5 stars

Overall rating 4.7 out of 5

Based on 316 authentic traveler reviews
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    5 out of 5 stars

    5/9/24 by 1st-time traveler Anonymous

    This was a fantastic trip. The cities and small villages that we visited were amazing. The people of Sicily were so friendly. Taormina was the best way to end, it was a beautiful city, wish we could have had more time there. The food all over Sicily was delicious. Our tour guide Rosa, was delightful...

    Read more +

    5 out of 5 stars

    4/6/23 by 1st-time traveler Carol

    Traveled all over the globe ... Go Ahead was the most organized and awesome travel group on every level ...

    5 out of 5 stars

    Sicily 2024
    6/7/24 by 6th-time traveler Minerva

    This tour to Sicily was wonderful. Rosa the tour guide was terrific and the bus driver Salvatore was an excellent bus driver. Locations were beautiful and the group wax one of the best we have traveled with.

    Show more reviews

    Traveler photos

    Hotels, flights & FAQ

    Here's the nitty-gritty—where you’ll stay, how you’ll get there, and what to know about your destination before you go.


    We handpick every hotel to strike the balance of comfort, location, and local charm. Specific accommodations will vary based on your departure date, but these are frequently used hotels for this tour and we're confident you'll be satisfied.
    Hotel Mercure Palermo Centro
    Hotel Mercure Palermo Centro

    This modern hotel is located in the Palermo city center. Guests enjoy free Wi-Fi, a bar, and a spacious lobby. Nearby, you'll find Teatro Politeama, T...

    Read more +
    Federico II Palace Hotel
    Federico II Palace Hotel

    This countryside hotel is located in Enna. Guests enjoy the indoor and outdoor pools, spa and elegant on-site restaurant. Nearby you’ll find the Vallo...

    Read more +
    Grand Hotel Villa Politi
    Grand Hotel Villa Politi

    This grand hotel is located near the historic archeological zone. Guests enjoy a restaurant, bar, and spa. Nearby, you’ll find the Greek Theater of Sy...

    Read more +
    Excelsior Palace Hotel Taormina
    Excelsior Palace Hotel Taormina

    This historic hotel is located in the city center. Guests enjoy an outdoor swimming pool, sun deck, and restaurant. Nearby, you’ll find Corso Umberto,...

    Read more +


    Round-trip flights are one more thing we handle to make your journey as smooth as possible. Our team of travel experts will find the best flight itinerary for you at a competitive rate, thanks to our partnerships with top airlines.
    Add our airfare package and you'll get:
    • Round-trip flight for your tour
    • Airport transfers at your destination
    • A great price locked in today
    • 24/7 support from our dedicated service team
    • Options for arriving early, staying longer, or requesting an upgrade
    • Flexible rebooking options if your tour itinerary changes
    • Find out more about flights


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