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 766 reviews
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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Zicasso's travel company planned the most amazing trip to Venice, Verona, Florence, Tuscany, Siena, and Rome for our family of five. It was the best trip I've ever taken, and having all the details covered by them and plans and tickets sent to us via WhatsApp allowed us to really live in the moment and not have to think about what was next. I loved every second. I cannot wait to plan another trip to Italy to experience the southern half of the country.
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"È stata una meraviglia!" Zicasso’s travel specialist crafted the perfect trip for us. Nothing “off the rack.” No cities. Just pure, unique, authentic Sicily! She was available any time we had questions and turned requests around in the snap of a finger. If you want to have dinner in the middle of the Mediterranean as you watch Stromboli volcano erupt in the night, the travel specialist will arrange it. She always presented us with the unexpected. Grazie mille!
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We had a great time in Sicily. All the tours and transports were on time and efficient. We had great tour guides who really helped us understand the history and many other things. If we needed help, Zicasso’s tour company was available to solve the issue.
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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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It was a pleasure working with Zicasso’s travel specialist and her team for our recent trip to Italy, including Rome and Sicily. The travel specialist was thoughtful throughout and demonstrated exceptional local knowledge when crafting our itinerary, particularly for Sicily, where we spent seven to eight days exploring the northwest, east, and southeast regions.
The itinerary beautifully blended visits to charming fishing villages with well-paced day tours, allowing for meaningful free time in between. In fact, she strongly encouraged us to include a free day to explore on our own, which made a noticeable difference, as we never felt rushed or exhausted. The hotels were impeccably selected and added greatly to the overall experience.
This was a truly memorable trip that we enjoyed every step of the way.
Thank you to the travel specialist and the travel company for creating such a wonderful experience. We will absolutely turn to them again for our next visit to Italy.
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