A Cultural Journey to Sicily Tour: Past & Present

Piazza del Duomo in Ortigia, Syracuse

What to expect on this itinerary

Sicily is a very distinctive region of Italy, filled with unique personality stemming from architecture that spans thousands of years. The coastline undulates between pristine beaches to remarkable cliffs. Mount Etna looms over wineries and cities, puffing smoke and spouting lava. Baroque palaces line charming piazzas. Marvelous frescoes decorate historic churches. Greek temples continue to stand tall along the edges of a modern city. Cobblestone streets twist and turn alongside medieval homes. Your custom tailored Sicily culture tour brings you to the unforgettable wonders of Sicily, embodied in the buildings, cuisine, and scenery scattered across the island.

Countries Visited

Italy

Places Visited

Palermo, Agrigento, Syracuse, Taormina

Suggested Duration

11 Days

Customizable Itinerary

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Day 1

Palermo - Introducing Palermo

Palermo’s uniqueness stems from its vibrant architecture, stunning setting, and radiant culture. The jovial calls of vendors at La Vucciria market echo off of the historical walls encompassing the stalls. “Vucciria” means voices in Sicilian dialect, and rings true in the boisterous and jubilant atmosphere of the marketplace. Produce native to the Mediterranean and North African climate thrives in both color and size. Herbs bring a sensual aroma to the pathways. Fresh seafood caught earlier that morning showcases the variety and abundance of what the oceans has offered residents of Sicily for millennia. Your private transfer greets you at the airport and escorts you to a luxurious hotel situated near the heart of the city. You quickly notice that the markets of Palermo offer more than just insight into the local shopping habits and vendor practices of the Italian province. They also embody the eclecticism of the cultures that have traversed and shaped the island.

What's Included:

Transfer
Accommodation
Day 2

Palermo - The Apparent Wonders of Palermo

Day 3

Palermo - Delighting in the Days of Palermo or Lampedusa

Day 4

Agrigento - Fascinating Greek Ruins in Italy

Day 5

Agrigento - Preserved Piazza

Day 6

Syracuse - Taking in Syracuse

Day 7

Syracuse - Deeper into the Splendor of Syracuse

Day 8

Taormina - The Draw of Taormina

Day 9

Taormina - Independent Taormina

Day 10

Taormina - Luxuries of Taormina

Day 11

Taormina - Taking the Culture with You

Trip Highlights

  • Experience the unique amalgamation of cultures that have settled in Sicily over a millennium
  • Discover lavish palaces and sensational cathedrals decorating the cities and towns across Sicily
  • Relish the tremendous marketplaces that offer insight into the daily lives of the locals
  • Witness the largest Greek amphitheater in Sicily located in the city of Syracuse
  • Revel in the stunning ancient Greek ruins located in the Valley of the Temples
  • Relax on an exquisite sandy beach edging the waters of the Bay of Naxos
  • Trek the lunar landscape of Mount Etna, Europe’s most active volcano

Detailed Description

Sicily is an island jewel in the Mediterranean, with coastal views that look out across the Strait of Messina to mainland Italy; in the other direction, you can see across the Tyrrhenian Sea to catch glimpses of the shores of Tunisia. The heritage of the island brims a blend of Phoenician, Greek, and Roman, and Carthaginian settlements, followed by Arab and Norman invaders. The blends of civilizations have made the culture of Sicily unique to Italy and the world. Each city has its own characteristics emanating from the architectural style and vibrant marketplaces. Your vacationing in Sicily begins when you arrive in Palermo, where your private transfer escorts you to a beautiful hotel located in the heart of the city.

The following day, you have a guided tour of Palermo and Monreale. The bayside city and architectural beauty of the provincial capital encompass the vast history of Mediterranean exploration by cultures from near and far. The cathedrals of Monreale show inspiring grace. The day is at your leisure to enjoy the city as you please, taking in the magnificent markets or winding through the interesting catacombs. The next day, you leave the capital city behind for the ancient Greek ruins located in the archeological park known as the Valley of the Temples.

Embrace the charming village of Piazza Armerina. The Roman villa outside of town contains a brilliant array of preserved mosaics. Your guide leads you on a majestic tour of Syracuse, once the largest city in the ancient world. Many ruins and antique buildings continue to decorate the cityscape. With a day in Syracuse at your leisure, you can visit the tremendous Greek theater or explore one of the 12 ancient quarries of the old city at Latomia dei Cappuccini.

Next, you travel to Taormina, where you have three days to enjoy the splendor of the town’s seaside location. Your guide leads you on a fabulous tour of the city’s charming streets, lined with palaces and the first seat of Sicilian parliament. Spend time on the opulent beaches on the fringes of Taormina, or escape to the high reaches of Mount Etna on a guided hike of the volcanic landscape. On your final day, your private transfer meets you at the hotel and transfers you to the Catania airport for your flight home.  

Starting Price

$5,000 per person (excluding international flights)

Your Zicasso trip is fully customizable, and this sample itinerary is a starting place for your travel plans. Actual costs are dynamic, and your selection of accommodations and activities, your season of travel, and other such variables will bring this budget guideline up or down. Throughout your planning experience with your Zicasso specialist, your itinerary is designed around your budget. You can book your trip when you are satisfied with every detail. Planning your trip with a Zicasso travel specialist is a free service.

What's Included

  • Accommodations
  • In-country transportation
  • Some or all activities and tours
  • Expert trip planning
  • 24x7 support during your trip

Your final trip cost will vary based on your selected accommodations, activities, meals, and other trip elements that you opt to include.

4.9

Verified Traveler Reviews

Based on 500 reviews

Italy Trip Review: Taormina, Agrigento, Palermo, 8 Nights

Our Zicasso travel specialist did a fantastic job planning our family vacation for five adults.

Each hotel was top-notch. At the villa in Taormina, the rooms were luxurious, with unbelievable views of the bay and Mount Etna from private verandas. The staff were gracious and the restaurant's breakfast buffet delicious. Lunch and dinner were top-notch. The hotel in Agrigento was modern and the grounds were exceptional. It was close to the Valley of the Temples, with amazing views of the ruins from each room and the beautiful infinity pool. The hotel in Palermo was old-fashioned luxury with up-to-date facilities and close to the old town.

Our tour guides and drivers were excellent.

My only regret is that we only had 10 days to explore Sicily as there was so much more to see!

Our agent did a yeoman's job helping us plan this trip.

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Sicily Vacation Review: Syracuse, Noto, Ragusa, Modica, Ortigia, 1 Week

We had a fabulous time in Sicily. It was our first visit and Zicasso’s travel company planned an excellent itinerary, with great recommendations on the cities and towns to visit that felt like a truly local experience. (Other agents focus on the big cities of Palermo and Taormina, but the travel company recommended we spend more time in Syracuse/Noto, Ragusa, and Modica.)

We loved our primary driver and the boutique hotels they selected for us. Communication and documents were all easy to follow.

The only piece we wish might have been curated a little more was the recommended dining options. There were too many and not necessarily great restaurants.

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Italy Travel Review: Rome, Ortigia, Modica, Agrigento, Noto, Marzamemi, Taormina, Winery Visit, Food Tour, Mt Etna, 9 Nights

Overall, I loved all that was planned for me by the travel specialist. She did a great job planning the transfers, tours, and activities we discussed during our planning. In particular, I loved my tour of Modica, the winery visit, my visit to Agrigento, and my visit to Noto and Marzamemi. I also loved my hotel in Ortigia - the location, the architecture, the views. I wish I had requested a sea view for my Taormina hotel, as not having that felt like a miss. I did not like at all the hotel in Rome (in spite of its convenient location) - it was a miss after such a glorious trip.

Every single tour guide and driver was excellent, knowledgeable and reliable. The initial personal fast track transfer in Rome was also excellent, and I requested the same service when I was leaving.

I would have liked the food and wine tour in Taormina to be a bit more elevated, given I am a foodie with elevated tastes. The local Sicily organizer, was very responsive overall. I just found it strange that she did not follow through on her offer to pay for a dinner because I chose my own venue.

The reason I am not giving this trip a 5 is because of a few issues: the room in Taormina and the hotel in Rome. The trip started strong with the transfer support and I wish it had been included at the end - I paid an additional fee for it. I also paid a significant additional fee for a private tour to Mt. Etna, which was given by the same person who drove me there. I feel like I overpaid for that tour. I canceled the Etna Food and Wine tour and wish I had gotten some consideration for that.

Stepping back, I am grateful for the trip and all the detailed organizing that went into it. I will look more closely at hotels offered so I avoid being disappointed.

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Italy Vacation Review: Sicily, Temples, Cathedrals, Cooking Class, Boat Tour, 2 Weeks
"Zicasso’s travel agency planned the trip of a lifetime for us. They were attentive, communicated with us daily, and responded to any concerns."

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Italy Vacation Review: Palermo, Ragusa Ibla, 20 Days

Zicasso’s travel agent and her team were very responsive when we needed assistance. We definitely didn't need three weeks in Sicily—there's not that much to see. Three of the hotels were great and two not so great, but again, the travel agent's team was quick to find us a better alternative. Thanks to the travel agent and her team.

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Italy Tour Review: Rome, Amalfi Coast, Taormina, Sicily, Sorrento, Capri, Mount Etna, Pizza-Making Class, Boat Ride, Wine, Local Cuisine, 9-Night Trip

We were absolutely thrilled with our first trip to Italy! This was a journey we had dreamed about for many years and we decided to make it happen as a special way to celebrate our anniversary this year.

The planning process with Zicasso was seamless, easy, and incredibly efficient. We were amazed by all of the thoughtfully planned activities, tours, and transfers throughout our trip. We visited Rome, the Amalfi Coast, and Taormina, Sicily—each destination offering something unique and unforgettable.

For this trip, we wanted a balance of adventure and relaxation, along with a few specific requests, and the team went above and beyond to make it happen. They truly bent over backwards to incorporate everything we envisioned and exceeded our expectations in every way.

We highly recommend traveling with Zicasso! They connected us with outstanding partners who truly elevated our experience and made our trip unforgettable. We honestly wouldn’t have changed a thing.

From the bottom of our hearts, Grazie mille!

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Customizable Itinerary

This is a sample itinerary to inspire a personalized trip designed with your travel specialist.

31,000+ Verified Traveler Reviews