Italy’s Greatest Cities Tour with Sicily

What to expect on this itinerary
Dreamlike escape filled with magnificent architecture, ancient ruins, delicious food, breathtaking art, and embracing natural scenery is yours to experience on this 11-day Italy and Sicily trip. From the Sistine Chapel to Michelangelo’s David, exuberant palaces to magnificent towers, your custom-tailored Italy tour with Sicily takes you to unforgettable cities, each brimming with historical delight and treasured enchantment.
Customizable Itinerary
Rome - The Greatness of Rome
Rome is Italy’s vibrant capital city, evoking a powerful ancient empire and a strong connection to legendary popes and artists. Cathedral domes add to the historic skyline. Narrow cobblestone lanes open up to hidden piazzas. The aroma of fresh pasta filters through a charming local restaurant specializing in family recipes passed down for generations. Ancient wonders lead to Baroque beauty. Your private transfer greets you at Leonardo da Vinci-Fiumicino Airport upon your arrival. Soon you find yourself in a luxurious hotel near the heart of the city.
The Arch of Constantine stands between the Colosseum and Palatine Hill. The 4th-century structure frames the Via Triumphalis; the pathway emperors took to enter the city after a military triumph. The arch stands more than 68 feet tall and 84 feet wide. It is the perfect image to welcome you to the city, flouting the grandeur of the ancient empire in the well-preserved friezes detailing the triumphs of the past.
What's Included:
Rome - True Splendor of Rome
Pisa - Continued Greatness of a Maritime Past
Florence - Immersion into the Renaissance
Verona - The Home of Star-Crossed Lovers
Venice - Looking Around the Lagoon
Venice - Power of the Este
Taormina - Onward to the Riviera
Taormina - Remarkable Riviera
Taormina - Endless Sensations of Sicily
Taormina - Fond Farewell to the Taormina
Trip Highlights
- Discover the exquisite sight of the Leaning Tower of Pisa and the surrounding splendor of the Piazza dei Miracoli
- Relax in the marvelous seaside atmosphere and sensational historic ambiance of the Sicilian city of Taormina
- Witness the unparalleled masterwork decorating the Sistine Chapel, a part of the Vatican Museum
- Tour around exceptional ancient Rome, taking in the Colosseum and Roman Forum on a guided tour
- Relish an intimate view of Michelangelo’s David on a private tour of the Academy of Fine Arts in Florence
- Explore the historic walls and famous grounds of the Este Castle in Ferrara
- Visit the charming courtyard of Juliet (from Shakespeare’s Romeo and Juliet) in Verona
- Traverse the majestic streets of Venice lining the romantic canals
Starting Price
$5,000 per person (excluding international flights)
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.
Verified Traveler Reviews
Based on 4746 reviews
I was very pleased with the entire planning of the trip. The communication with Zicasso's tour company was excellent. The meals that were pre-arranged by them were fantastic and we probably would not have found them on our own.
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Our trip was absolutely amazing! This was the trip of a lifetime. Zicasso and our trip planner were incredible. He was repeatedly helpful, offering personalized attention to our needs. He booked amazing tours for us and seemed to really grasp what we wanted. Everything was incredible.
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My husband and I had a great time on our trip to the northeast Adriatic Coast of Italy. We have very specific tastes as far as where we like to stay and the private tours we like to have during the trip. Zicasso's travel company did a great job, giving us fantastic hotels, and all of our tour guides were top-notch.
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Zicasso's travel agency planned the trip of our dreams! We spent 10 wonderful days in Italy, and it was the perfect mix of activity and leisure. We loved our accommodations and everything ran seamlessly. All the transfers and reservations were arranged and executed without any issues. Our travel agency was very responsive throughout the planning process and while we were on the trip. I would absolutely recommend their services and feel really grateful for the experience we shared.
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I am very happy that we chose this Zicasso travel agent. He was very responsive throughout the evaluation and planning process, as well as while we were traveling, with any questions we had. He checked in during our trip to ensure things were going smoothly and we asked his advice via WhatsApp a couple of times during our stay in Greece, to which he responded quickly and immediately researched our request.
Every transfer was on time and all of the tours were high quality. I really can't think of anything we weren't pleased with in terms of his service!
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The trip of a lifetime–thanks to Zicasso's travel company!
We recently had the absolute best travel experience of our lives, and it’s all thanks to the incredible team at this travel company. Words can hardly capture how grateful we are for the magic they created for our trip to Greece.
We were headed to a friend’s wedding on Paros and trying to plan the logistics ourselves quickly became overwhelming; figuring out how to get there, what to do, and where to stay felt impossible. That’s when my husband found this company and, from the very first interaction, we knew we were in good hands. They took the time to really get to know us, what we enjoy, our travel style, our budget, and how hands-on we wanted them to be.
After a few thoughtful conversations and a video call, they crafted multiple itinerary options tailored exactly to our preferences. In the end, we landed on a perfect blend of history, fun, and relaxation. They even helped us work everything around the wedding, ensuring we didn’t miss a thing.
We started our journey in Athens, landing early in the morning and diving straight into the day. Then came one of the highlights of the trip—meeting our travel agent in person. She met us with the warmest welcome, walked us through our itinerary, personally showed us around the city, and gave amazing recommendations for food and shopping. Her kindness, energy, and passion for hospitality were contagious.
But what truly set this company apart was their level of care and communication. Throughout our entire trip, they were just a WhatsApp message away. They proactively checked in before every activity, sent us all the necessary contacts for transport and tours, and made sure we felt supported every step of the way. Every place we stayed at was breathtaking. From Athens to Paros, Milos, and Naxos, each hotel was more stunning than the last. Immaculate rooms, beachfront views, and hosts that treated us like family. The breakfasts were absolutely mouthwatering and gave us the perfect start to each adventure-filled day.
Beyond the wedding festivities, our itinerary included food tours, temple visits, an unforgettable catamaran tour, and a dreamy sunset cruise. Every single moment felt like a dream. The islands are incredibly safe, perfect for solo travelers or a girls’ getaway, and the views? Just… wow!
And the food! I cannot emphasize this enough: the food was out of this world. Every meal was a delight—fresh, flavorful, authentic, and somehow we left feeling better than when we arrived (even after eating three generous meals a day, with snacks in between!). Pure magic.
I’m already counting the seconds until we can go back. This trip exceeded every expectation we had and gave us memories we’ll treasure forever.
To top off this unforgettable trip, we decided to spend a few days in Rome—and the travel company helped with that too! It was the perfect ending to our adventure. We explored the Vatican, the Colosseum, the Roman Forum, and the Pantheon. Every site was awe-inspiring and the city’s energy was just electric. Rome was the cherry on top of a journey we will never forget.
To the entire team—thank you from the bottom of our hearts for the most unforgettable adventure of our lives. We wouldn’t dream of traveling to Greece again without you.
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