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 592 reviews
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.
See more
We had a fantastic experience for a first-time trip to Italy. I wasn't sure how this would be, considering I learned about Zicasso while trying to plan the trip myself. Zicasso put me in touch with a travel specialist and the whole team was incredibly responsive to my many, many questions. If they were ever annoyed, it didn’t show.
I really wanted a smooth experience for my family of five, including three teens, one of whom has Celiac. Our agent was great in helping plan out the experience we wanted. As you may know, it is challenging to find rooms for five in Europe, but the travel company found apartments (usually two bedrooms with a pull-out couch) in the heart of town. You can really customize what you do, but we elected to plan our own meals and handle some of our own transport. We did have one issue where the van driver taking us to the train failed to show. I got one with Uber and the travel company quickly (I mean before we got home quickly!) refunded that amount.
Our contact in Italy was amazing and patient. I can’t give her enough credit. Any time I was unsure of something, she was there. The tours were great, especially Florence and Rome. You may be able to find the companies online, but ours seems to have the connections to get the best guides.
As for meals, we didn’t have any issues. We used an app and got a few recommendations from the travel company and local guides. Even our wine-tasting tour out in Tuscany was accommodating.
I would use our travel company and Zicasso again. I think the only downside is we tried to cram a lot in and it was hot. I probably should have asked for one to two fewer or shorter walking tours, especially on days we switched cities. Otherwise, it was excellent.
See more
From the moment we began working with Zicasso's trip planner, our every need was met. He listened and planned an epic trip based on our conversations. Then, for our trip, we worked with another trip planner who was extremely responsive and professional, especially when we were in Italy. Any questions we had were promptly answered. Everything they planned was pure luxury and fantastic. The private pick-ups, drivers, and tour guides were absolutely prompt and fantastic. Every tour was super-fun and informative. Highlights included the wonderful hotels, food tour in Florence, tour in Venice, cooking class, and tasting track in Tuscany. I would highly highly recommend. It was a five-star, wonderful trip!
See more
We loved Sicily! Zicasso's travel operator provided us with an amazing trip! Every guide and activity surpassed our expectations. From the archaeological parks to the cooking class at the palace, the art class, the Jeep tour of Mount Etna, the olive oil and lemon farm, but especially the guides she selected for us, it was pure joy! The history of that country is mind-boggling and fascinating to learn about.
See more
See more
The trip itself was OK. We loved getting to know Sicily and the itinerary provided by Zicasso's travel company was very interesting. The suggestion I would make for new travelers to this region is that they choose another time, instead of May. We expected warmer weather.
Another suggestion is that if you are going to rent a car, choose a small one. The cities are really small (downtown), so the streets are very narrow. You have to be very careful when driving. In Ragusa, a parking lot near the best part of the city should be recommended (I have already told the travel consultant about that).
As for the rest, everything went just fine and I would recommend visiting Sicily.
See more





