Exclusive Christmas in Italy Tour: Rome, Florence, Milan

What to expect on this itinerary
From a graceful Christmas tree contrasting the powerful Colosseum walls to the vibrant display of lights accentuating Nativity scenes decorating the streets of Florence, Italy provides a holiday season brimming with welcoming, cheerful ambiance for all to enjoy. Discover the beauty of Pisa in December as seen from the top of the Leaning Tower and absorb the splendor of a New Year’s Eve performance at the famous La Scala Theater in Milan. Your customizable tour immerses you in Italian culture and illuminates the deep-rooted connection between ancient tradition and Christian heritage embodied in Italy’s art, architecture, cuisine, and customs.
Customizable Itinerary
Rome – An Eternal City in Season
The thrills of Rome emanate from the ancient ruins, commemorating a lavish past and the remarkable spires of historic churches offering images of the Vatican’s influence in the city and across Italy. During the holiday season, Rome radiates cheer from the dangling lights crisscrossing above historic cobblestone streets and Christmas markets filling famous piazzas. Your flight lands at Rome Fiumicino Airport. Your private transfer greets you at baggage claim and escorts you to a luxurious hotel located in the heart of the historic city center.
The ancient frame of the Pantheon comes into view. The 16 thick pillars frame the entryway and support the edge of the massive dome, which reaches a height of 142 feet above the streets. Your guide meets you in the hotel lobby, eager to introduce you to the beauty of Rome glowing in the Christmas lights. You make your way to the Colosseum, the iconic image of the Roman Empire’s strength. Your guide helps contrast the rituals of the pagan religion of the city’s past with the deep connection of Rome’s Christian tradition.
The outer walls of the Colosseum reach four stories tall at a height of 157 feet. A canopy once spread across the seats casting shade over spectators. The archway frames the hall that soon swallows you, opening to the center of the remarkable structure. You can look down into the labyrinth, above which the wooden stage once stood. Gladiators would train, and wild animals would pace their cages, both waiting their turn to enter center stage.
What's Included:
Rome – A Roman Christmas Eve
Rome – A Holly Jolly Christmas Day
Florence – Markets of the Renaissance
Florence – Enchanting Tuscan December
Florence – Themes from the Art World
Florence – Into the Christmas Culture of Pisa
Milan – The Lights of Cinque Terre
Milan – A Fashionable New Year’s Eve
Milan – A New Year’s View of Italy
Trip Highlights
- Experience the unique pleasure of attending midnight mass in St. Peter’s Square, as presided over by Pope Francis
- Discover the joyful holiday season embodied in the thriving Christmas markets of Rome and Florence
- Relish the country charm and splendid history of the medieval Siena, located in the southern hills of Tuscany
- Explore the unique connection between the Roman Empire’s traditions and the heritage of Christianity on a private tour of Rome
- Immerse yourself in the Christmas culture of Florence with a tour of the Renaissance city’s historic and lavish churches
- Delight in a distinctive New Year’s Eve celebration with a remarkable dinner followed by a celebratory evening in Milan’s elegant La Scala Theater
- Traverse the grounds of the Sacred Field in Pisa, where soil from Calvary (where Christ was crucified) was brought back during the Crusades
- Stroll the hillside trail of Manarola alongside the extravagant Nativity scene of 250 characters cloaked in lights, which overlooks the Mediterranean Sea
Detailed Description
Discover the cheers and traditions of Italy in December during your 10-day tour of encompassing Christmas and New Years in the cities of Rome, Florence, and Milan. The remarkable journey begins with your arrival in Rome. Your private transfer meets you at Rome’s Fiumicino Airport and escorts you to a luxurious hotel in the city center. Your private guide leads you on an introductory tour through Ancient Rome, which includes the Roman Forum, the Colosseum, and Palatine Hill. Learn about the ways the past has influenced the present through customs and traditions. The next day is Christmas Eve and Rome buzzes with excitement. Wander through the Christmas markets and see the detailed Nativity scenes in Piazza del Popolo. In the evening, you venture to St. Peter’ s Square to attend midnight mass led by his Holiness, Pope Francis.
On Christmas Day, you have a private tour of the city’s connection to Christmas, walking through the history and tradition along the cobblestone alleyways and open piazzas. In the evening, you partake in a superb Italian Christmas dinner. You have a first-class seat on the train north to Florence the next day. Your private transfer escorts you to a luxurious hotel in the historic city center surrounded by Renaissance palaces and glowing holiday lights. Explore the distinct churches filled with unforgettable art and unique stories as shared by your private guide. The following day, enjoy a full day tour of Siena; wander along the festive atmosphere inside the medieval city walls. Visit one of the oldest hospitals in Europe at the Santa Maria della Scala Museum, which now contains stunning exhibits telling the detailed history of Siena through its art.
Next, you explore the art of Florence, beginning with the Uffizi Gallery, for a better understanding of how classics and early Christian allegory inspired the works of master Italian artists through history. The following day takes you into western Tuscany to discover the holiday spirit in the cities of Pisa and Lucca. Visit the Sacred Field and gothic churches of Pisa before climbing to the top of the Leaning Tower. Enjoy the holiday ambiance of Lucca inside the medieval city walls encircling the city before returning to Florence. Then you travel north to Milan, the capital of the Lombardy region. You have the option of visiting the coastal villages collectively known as Cinque Terre. The town of Manarola contains a stunning Nativity scene with 250 characters radiating with light against the hillsides in the evening.
Then it’s New Year’s Eve. The day is yours to explore the fashionable and industrious city of Milan at your leisure. Visit the La Scala Opera Museum or tour the church of Santa Maria delle Grazie to see da Vinci’s Last Supper. In the evening, you can bask in a delectable meal before embarking on a thrilling night at Milan’s famous La Scala Opera House. On the final day, you can unwind and bask in the serene quiet of New Year’s morning. Extend your stay in Italy for a magnificent time in the Dolomite villages or a sun-drenched start to the year in the Sicilian resort town of Tamarindo. Your private transfer meets you at the hotel in Milan when you are ready and escorts you to Malpensa Airport for your flight home.
Starting Price
$9,800 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 637 reviews
Zicasso’s travel company and every single guide and driver were stellar. All four hotels were good or excellent. There was one error on the schedule for the day outside of Florence when we had a driver to take us to the Siena region. The schedule stated three hours, so we paid for tickets to the Pitti Palace/garden, which turned out to be wasted money as the driving tour was actually nine hours. It was a beautiful day, though.
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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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The drivers were timely, professional, and very prompt. The guides were very knowledgeable and generally designed the tours to match our requests. The hotels were exceptional and our only comment is that there was an odd odor in our room in one of the hotels.
Our only true complaint would be about the wine tasting on May 22. The location was not aware of our reservation. The couple running the vineyard seemed confused by our arrival. After a bit, they offered to accommodate us, but we felt like we were imposing on them. Then, at our lunch at a restaurant on Capri, they did not have a record of a reservation and placed us at a table without a view, near the entrance. We made the best of the meal, but for the price we paid, we would have expected confirmed reservations and a table with a view.
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We've taken many family vacations over the years, but we all agreed this was the best one yet!
The team at Zicasso’s travel company did an exceptional job tailoring the perfect trip for our family. Every detail was thoughtfully planned, making the entire experience seamless and truly enjoyable from start to finish.
We had wonderful drives and knowledgeable, engaging tour guides who made each destination come to life. Some of our favorite highlights include a hands-on cooking class in Florence, exploring the beautiful Tuscan countryside, and having effortless access to iconic sites like the Vatican and the Colosseum.
The experiences were unforgettable, from the best food tour in Rome to a fun and unique golf-cart tour through the city. We also loved visiting a Parmigiano-Reggiano factory and a Parma ham producer, along with an extra-special stop at the Ferrari Museum that was such a memorable surprise.
Every moment felt thoughtfully curated and we came home with incredible memories that we will cherish for years to come. We highly recommend the travel company to anyone looking for a truly personalized and exceptional travel experience.
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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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We had a great trip to Florence, Tuscany, and Rome. One of the best parts about the trip was our travel company. Zicasso's travel specialist took care of booking everything we needed and doing so within budget. I didn't have to worry about keeping up with tour tickets and schedules because he had already taken care of all that. He was also available for quick questions and updates while we were on our trip. We couldn't have asked for better!
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