Italy’s Greatest Cities Tour with Sicily

Doge's Palace, Campanile, St. Mark's Basilica and St. Mark's square in Venice, Italy

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.

Countries Visited

Italy

Places Visited

Rome, Pisa, Florence, Verona, Venice, Ferrara, Taormina, Sicily

Suggested Duration

11 Days

Customizable Itinerary

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Day 1

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:

Transfer
Accommodation
Day 2

Rome - True Splendor of Rome

Day 3

Pisa - Continued Greatness of a Maritime Past

Day 4

Florence - Immersion into the Renaissance

Day 5

Verona - The Home of Star-Crossed Lovers

Day 6

Venice - Looking Around the Lagoon

Day 7

Venice - Power of the Este

Day 8

Taormina - Onward to the Riviera

Day 9

Taormina - Remarkable Riviera

Day 10

Taormina - Endless Sensations of Sicily

Day 11

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)

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 742 reviews

Italy Family Vacation Review: Venice, Verona, Florence, Tuscany, Siena, Rome, Biking, Cooking, Wine Tasting, Olive Oil Experience, 10 Nights

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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Italy Vacation Review: Sicily, Cooking Class, History, 12 Nights

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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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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Italy Trip Review: Rome, Sicily, 12 Days

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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Italy Trip Review: Rome, Venice, Florence, Opera, Walking Tours, 10 Nights

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.

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Italy Trip Review: Milan, Florence, Lake Como, Venice, 11 Nights

When we started planning our trip to Italy, I knew I wanted to work with a travel agent—specifically, someone who specialized in Italy and was based there. After reaching out to several agencies and reviewing their responses, we chose Zicasso and, more specifically, our travel agent. She is based in Milan and from my very first interaction with her, I knew we had made the right choice.

Our trip could not have been more perfect. Our agent put a lot of thought into every location and planned activity. At the outset, we had a few discussions with her about what we wanted from the trip and, after that, we were happy to leave most of the details in her capable hands. Our goal was to explore mid-to-northern Italy and everything—from the hotels and tours to the free time and transportation—was beautifully organized.

Our 11-night trip started in Milan and ended in Florence, with overnight stays in Milan (one night), Lake Como (three nights), Venice (three nights), and Florence (four nights). Initially, I was hesitant about staying at Lake Como for three nights, but our agent encouraged me to do a little research. I’m so glad she did, as it turned out to be incredible. We had more self-guided time at Lake Como, which was perfect as we adjusted to the time change. In Venice, our itinerary became more structured, but we still had plenty of time for our own explorations. By the time we reached Florence, we had activities and tours planned for every day, which was just what we wanted.

A highlight for my family was a full-day trip into Tuscany, where we visited San Gimignano, an organic vineyard in Chianti, and finished with a tour of Siena. Our day trip to Rome allowed us to see the main attractions and we concluded the journey with a tour of Florence and the Accademia Gallery. Every tour our agent arranged was spot on.

Throughout our trip, she was wonderfully communicative—always available when we had questions, but never intrusive. She even helped us with a couple of last-minute requests: booking a hotel in Milan for one night and arranging train tickets to Verona for an impromptu visit to Juliet’s balcony. Whenever we needed something, she was there.

When we return to explore the mid-to-southern part of Italy, there’s no question that we’ll be asking her to plan our trip again. I highly recommend her to anyone looking for a seamless, thoughtfully curated Italian adventure.

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Customizable Itinerary

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

30,000+ Verified Traveler Reviews