Exclusive Christmas in Italy Tour: Rome, Florence, Milan

St. Peter's Square at Christmas, Vatican City

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.

Countries Visited

Italy

Places Visited

Rome, Florence, Milan

Suggested Duration

10 Days

Customizable Itinerary

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Day 1

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:

Transfer
Accommodation
Breakfast
Day 2

Rome – A Roman Christmas Eve

Day 3

Rome – A Holly Jolly Christmas Day

Day 4

Florence – Markets of the Renaissance

Day 5

Florence – Enchanting Tuscan December

Day 6

Florence – Themes from the Art World

Day 7

Florence – Into the Christmas Culture of Pisa

Day 8

Milan – The Lights of Cinque Terre

Day 9

Milan – A Fashionable New Year’s Eve

Day 10

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)

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 496 reviews

Italy Tour Review: Capri Private Boat Cruise, Wine Tasting, 10-Day Vacation

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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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 Vacation Review: Cooking Class, Wine Tasting, 1-Week Tour

We loved all of our drivers and tour guides, and had a wonderful trip. We especially enjoyed the cooking class and the wine tour and tasting. 

We were disappointed in the restaurants booked for us on December 24 and 25, and would not recommend them to future guests. Our Christmas Day lunch was outrageously expensive and the food was not excellent. It began with our server telling us that prices would be 20% higher because it was Christmas and they were not doing flambé. They also did not have a full bar to order the drinks we wanted. We should have known that on the front end. There were plenty of restaurants open in the city and we would have had a much better and more reasonably priced meal elsewhere. We found a restaurant that we loved and went to several times. The service was outstanding and the food and wine were superior. We recommend it.

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Italy Grandparents and Grandson Vacation Review: History, Private Guides, 12 Nights

Zicasso’s tour operator did a fantastic job at making our trip to Italy with our grandson, aged 12, a success! The pace of our trip was perfect and we were able to see everything on our list. Our private guides took an extra-special interest in engaging our grandson and answering his many questions, since he is a history lover.  

Our hotel accommodations were lovely and tailored exactly to what we requested. The pace of the trip was very nice, so we had time to see everything, but we also had some downtime to relax and enjoy some time on our own.

Our drivers and transportation were very prompt and courteous. The vans and cars we rode in were all very clean. 

We had a wonderful time in Italy over Christmas and New Year!

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Italy Trip Review: World War 2 Sites, Piazza Armerina, 2 Weeks

We had an excellent time. The drivers and guides were all on schedule. The hotels were clean and comfortable. The tour was exceptional in the variety of sites offered and information provided.

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Italy Trip Review: Rome, Siena, Orvieto, Venice, Pienza, Vatican, Colosseum, Roman Forum, Vespa Tour, E-Bike Tour, 10 Nights

Our trip to Italy was amazing! The tours that were organized for us were all excellent and engaging. 

The Vespa sidecar tour was an incredible way to kickstart the trip and our two teenage boys really enjoyed it. Our walking tours of the Vatican museums and the Colosseum and Roman Forum tours with our guide were excellent. We loved her. She was fantastic. Our tour of the crypts and catacombs was very interesting and the guide was very good.

The hotels were very nice and accommodating, especially in Rome and Venice. The car rental in Rome was good and the car was the perfect size for what we needed. It was just big enough to fit our luggage. 

The hotel in Orvieto was a bit spartan and had plumbing issues. Our tour guide in Orvieto was also great. The hotel in Siena was very nice. Our tour guide in Siena was very nice, but we had some difficulty hearing her. She did explain things nicely and took us to some interesting locations around the city, but not being able to hear her was a little challenging. The e-bike tour in Montepulciano was incredible. The scenic landscapes and the visit to Pienza was a nice surprise. 

Returning the car in Florence was very difficult and our only suggestion is that on the travel documents, the return address be included on the page of the event. We did not think to look back at the rental agreement. Driving in Florence is very difficult and can be overwhelming for some people. 

The train station was organized and it was easy to locate the train. The train ride itself was very easy and fast. 

Venice was outstanding. Our hotel was beautiful and comfortable, and the breakfast was incredible. Due to the difficulty we had in returning the car in Florence, our travel company was kind enough to buy us dinner at an wonderful restaurant in Venice, which was one of the highlights of the trip. 

Our family had a wonderful experience and the trip was so well planned and organized. I will be using our travel company for future trips and, on behalf of my family, I would like to thank you for the time of our lives!

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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