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 1242 reviews

Italy Tour Review: Sicily, Taormina, Agrigento, Palermo, Cefalu, Mount Etna, Erice, Castelbuono, Savoca, Valley of the Greek Temples, Wine Tour, Godfather Experience, Farm Cooking Class, Cheese and Pastry Tastings, 7 Nights

Zicasso’s travel professional crafted an unforgettable Sicily trip for our group of seven. After discussing our preferences, she designed a flawless itinerary, incorporating unique experiences that became trip highlights. Her communication was exceptional, with prompt responses to our questions before the trip and daily updates for the next day's activities, including driver and guide details, which were incredibly helpful.

We stayed at superb hotels in Taormina, Agrigento, Palermo, and Cefalù, each with stunning views and private tours. Sicily’s warm, hospitable people stood out compared to other European destinations. At our hotel on Via Leonardo da Vinci in Taormina, the staff greeted us warmly, setting a perfect tone. Other stops included Mount Etna, Erice, Castelbuono, and Savoca. All of these locations were great, but don't miss Castelbuono!

Two standout experiences were private meals with families. Near Erice, a chef and his family welcomed us into their sea-view home, preparing amazing Sicilian meals that felt like dining with family. In Palermo, another home chef and her husband created a similarly memorable evening, with lots of great conversation and stories.

Every driver was professional, friendly, and informative, while our guides — often archaeologists or historians — were engaging and knowledgeable.

Highlights included a welcome dinner in Taormina, a farm cooking class, two wine tours with lunch, a Mount Etna hike, a Valley of the Greek Temples tour, town and village tours, cheese and pastry tastings near Cefalù, and a farewell dinner. The Godfather tour in Savoca was special, with our guide introducing us to a local who played Apollonia’s mother, waving from her balcony.

Our travel professional's meticulous planning and personal touches made this trip extraordinary. Thanks to Zicasso for matching us with the tour company and we highly recommend them for a perfect Sicilian/Italian adventure!

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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 Travel Review: Taormina, Syracuse, Catania, Militello, Ragusa, Aci Castello, Modica, Mount Etna, Private Tour, Cooking Class, Boat Ride, 9 Nights

This was a superb trip that allowed us to combine personal visits to Taormina and Syracuse with a pre-planned group meeting in Catania. Planning and communication were excellent, supported by an app that let us easily view our itinerary, complete with phone numbers for the drivers, hotels, and the tour operator contacts.

The hotels were perfect! They were wonderfully located, with impeccable service in Taormina and Syracuse. Our excursions were private and diverse, and allowed us to combine culture, foodie interests, and free time. The guides were top-notch, knowledgeable, and flexible.

We especially loved seeing the smaller towns of Sicily; Militello, Ragusa, Aci Castello, and Modica. We even arrived in one small town during their annual festival.

We had a dedicated driver for our trip who was, himself, a treasure; always on time, always ready to adjust to changes, and a delightful personality.

This was such a good experience that we have selected Zicasso's tour operator to book another Italy trip next year.

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Italy Vacation Review: Pompeii, Capri, Amalfi Coast, Mount Etna, Taormina, Godfather Tour, Boat Day, Opera, Winery, 2 Weeks

Overall, the trip was fantastic! The hotels in Italy and Sicily were awesome. Most tours were five-star!

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Italy Vacation Review: Palermo, 10 Nights

The travel company and staff were excellent. The trip coordinators accompanied us through the trip via WhatsApp. They were terrific. The service was top-notch, including the drivers, tour guides, and accommodations.

The one thing I would change about the trip is to have longer stays in each city visited. Moving to a new hotel every two nights prevented us from really enjoying each city we visited. I would also forgo Palermo and substitute a smaller city like Noto or Agrigento. But again, the itinerary was based on my interests and time. It is not an indication of the tour company's abilities. However, it may be good for the agency to suggest longer stays to other customers. Otherwise, we had a great trip and once again, I have recommended Zicasso and the tour company to family and friends.

Thank you again for a great time!

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Italy Tour Review: Abruzzo, Pescara, Chieti, Venice, Verona, Lake Como, Milan, Turin, Cooking Class, Opera, Boat Ride, Food Tour, 12 Days

This was my third customized trip with Zicasso. I previously worked with Zicasso to plan and take mother-daughter trips to Iceland and Croatia. They are the perfect company to help your dreams for a personally unique adventure come true!

This time, I traveled with my daughter, son, and daughter-in-law to Italy. My hope was for my daughter and son to see the towns where their great-grandfather and great-grandmother emigrated from in the Abruzzo region, in the towns of Roccamontepiano and Bugnara. My research had an address for where their great-grandfather was born. Our driver found the address and we took photos of us standing in front of the house, which could now be considered a real fixer-upper. Just the same, it was a moment never to be forgotten. Thank you to our driver and his wealth of information!

Our home base was in Pescara, where we enjoyed a walk on the beach, excellent local cuisine at a local restaurant, and seafood at another local restaurant. These were recommended by our local travel agent and were clearly favorites of the locals.

We had a wonderful tour in Chieti, an historic and cultural gem, with our guide. She too was a gem of a guide!

We then traveled to Venice, which was far less crowded with tourists than in the high season. Upon arrival, a private gondola ride during dusk and at sunset was a surreal way to be welcomed to this beautiful city.

The next day we had a magnificent tour of St. Mark's Basilica and Doge's Palace. Our guide was so engaging and knowledgeable, and eager to share ideas about other things to see while in Venice. We followed our tour with lunch at a historic restaurant, home to the invention of the Bellini. Yum! After lunch, we took the elevator to the top of the tower across from the basilica, with its spectacular panoramic view of the city and surrounding islands. Then our group splintered off—two of us did a Grand Canal boat ride and the other two headed to the isle of Murano to search for glass souvenir treasures.

Our next stop was Lake Como, with a one-hour unexpected stop in Verona. Thank you to our driver for suggesting the stop! Who knew there was a Roman arena and some to-die-for hot chocolate in Verona!

Then off to Lake Como. We had time before we could check in to our hotel, so we did a walkabout to acquaint ourselves with the city. We took a ride on the funicular for another delightful panoramic view and enjoyed cocktails while surveying the lake and city below. That evening, we traveled up into the mountains and had a marvelous meal at a mountain trattoria. We were just us and one other couple in the restaurant, and we watched the chef prepare our local food specialties from our table in front of the wood-burning fireplace. The mantel was adorned with trophies and photos of the local bocce teams over the decades. Again, if you want to travel for cibo delizioso, go to Italy!

The next day, we had a three-hour boat ride on Lake Como. Our skipper and guide made certain to point out and give some history on the villages dotting the coastline and the famous villas.

The following day we traveled north to Domaso for an afternoon at a family-run vineyard and restaurant with views of Lake Como and the Alps! Bellissimo! A family member gave us a wonderful tour of the history and the winemaking facility, as well as the many wines we sampled. We were treated to local charcuterie and ravioli that was made fresh while we were busy sampling. When we received the wine we ordered and shipped back home, they threw in extra gifts for us, with wishes for a Merry Christmas and Happy New Year!

Then we were off to Milan for a chance to try our luck at making our own pasta, sauces, and gelato at a cooking school. Our chef instructor guided us as we made tagliatelle with a pesto sauce and pumpkin ravioli with a cream sauce. Of course, there were wine pairings! He made certain our creations were delicious!

That evening, we donned our fancy apparel and headed to La Scala to take in the opera, "Così fan tutte." The modern take on the comedy was refreshing and the venue was a must-see!

The next day, we were met by our guide, who shared the history of the UNESCO site of Santa Maria delle Grazie and Leonardo da Vinci’s "Last Supper" with expertise and reverence, while keeping us engaged. She likewise inspired us as we toured the Duomo di Milano, San Maurizio al Monastero Maggiore, and the controversial Il Dito sculpture outside the city’s stock exchange.

That evening, we experienced a delightful meal at a Michelin-starred restaurant. The chef, from Naples, created and explained a never-to-be-forgotten bite-sized sampling plate highlighting the tastes of Naples on a plate shaped like the region, with its various borders.

Before leaving Milan, we had a tour of La Scala and its adjacent museum with our guide. She provided us with a history lesson that was quite interesting. That night, we dined at a local seafood restaurant, another treasure clearly favored by the locals. Our waiter was a gem and sent us off with the gift of a bottle of wine.

Our final stop was Turin. Once again, we divided—two of us visited the National Museum of Cinema and the panoramic lift housed in the museum. At the top, we gained a wonderful sense of the city,and the cinema museum was a fun surprise! Our other two toured the Juventus Museum and Stadium, and they thoroughly enjoyed their experience as well.

Our final day, we met our guide, who spent the entire day with us, with only a short break, beginning with a gourmet food tour of traditional Piedmont dishes. Along the way, she shared insights into the history and cultural significance of the foods. Later in the day, she guided us through the Royal Palace of Turin, including the Holy Shroud Chapel, Armory, and Museum. Once again, we were treated to a knowledgeable and entertaining guide.

We departed the next day, leaving with priceless memories of our Italy adventure.

Thank you so much to Zicasso’s travel agent. You helped make our trip come true with such care. Grazie mille!

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Customizable Itinerary

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

28,000+ Verified Traveler Reviews