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 973 reviews
We had a lovely tour of Sicily and we thoroughly enjoyed the scenic villages, mountains and coastal areas, the delicious food, the history and culture of the region, and, of course, the many lovely Sicilians we met on our journey! This was made possible by the travel company we went with when we first engaged Zicasso. They met with us (online) and developed a great tour, for which a few highlights are summarized below. They were also very helpful during the trip to offer us assistance if we needed it. In short, they made our trip truly memorable!
On our visit to Palermo, we experienced its ancient history and fine cuisine. Touring some of the smaller towns and villages, such as Cefalù, Modica, Scicli, Marzamemi and Noto, we enjoyed many scenic streets and alleys with their many shops and restaurants, and also seeing some beautiful artwork in their ancient cathedrals. The countryside of Sicily is also lovely to see and on our tour, we were privileged to visit some farms and talk with some locals who make their living off the land.
We were captivated by the rich historical underpinnings of Sicily, as we saw when we toured Agrigento to visit the Valley of the Temples. In other larger towns/cities we visited, such as Ragusa, Syracuse and Taormina, we had many opportunities to tour food markets and taste (and to learn to prepare) some specialty dishes of the local area.
Having a walking tour around Mount Etna with a local guide provided us with a refreshing outdoor nature hike that was a great way to learn about the area. Capping off our nature walk with a gastro/wine tour at a local winery was a great finale to our two-week vacation! In the end, our only regret was that we didn't want the vacation to end!
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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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The cities we visited were wonderful. We really enjoyed the tours, especially the cooking class with our chef! I will be making homemade ravioli over the holidays.
The hotels were located close to the city centers. But the hotel in Bologna was very close to the university, with lots of graffiti and live music late into the night. The hotel, however, was quaint and very nice. The hotel staff was very friendly and accommodating.
The hotel in Florence was just weird. Our travel companions' room had no windows and was small. Ours was oddly laid out but much bigger. The desk person told us both rooms were the same when we first checked in. If we came back after 9 p.m., there was no hotel staff, and we had to use a code to walk through an apartment lobby.
The hotel in Venice was situated right in the middle of lots of restaurants and gelato! The hotel was by far the best one, with much nicer amenities and rooms. It had a bar and restaurant on-site. It was a good way to end our trip.
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Overall, I loved all that was planned for me by Zicasso's 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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My wife and I spent two weeks in Sicily and four more days in Rome. The trip was seamless: no glitches and no problems. Zicasso's travel specialist and others were promptly responsive, friendly, and cooperative. They made excellent suggestions and respected our preferences.
The transportation and the guides were all very good. The hotels were appropriate for our desires and budget. They provided wonderful sunset cruises in Palermo and Taormina, and they got us restaurant reservations for dinner each night at non-touristy places.
Surprisingly to us since we have been there before, Rome was especially enjoyable. The art in the Borghese Gallery and in the Pope's museum at the Vatican was overwhelming.
My wife and I have traveled extensively, particularly with agents obtained through Zicasso. They have all been good, and this one was one of the best. I can recommend our travel company without reservation.
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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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