Exclusive Christmas in Italy Tour: Rome, Florence, Milan

A 10 day trip to Italy 
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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.

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General Information

St. Peter's Square at Christmas, Vatican City
David di Michelangelo, Florence
St. Peter's Basilica, Vatican City
Detailed Itinerary

Places Visited 

Rome, Florence, Siena, Lucca, Pisa, Manarola, Milan 

Departure Dates 

Travel dates for this itinerary are December 23, 2017 - January 1, 2018, but dates are flexible and customizable for private departures. 

Detailed Itinerary 

Day 1: Rome – Dec. 23rd – 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

Day 2: Rome – Dec. 24th – A Roman Christmas Eve

In the morning, the scent of freshly brewed espresso emanates from the cafes set across the city. The fragrant aroma of freshly baked panettone, seasonal bread sweetened with honey and raisins, emanates from bakeries and shops. After breakfast, your guide meets you at the hotel and leads you through the festivities of Rome on a jovial Christmas Eve. The Christmas Market in Piazza Navona overtakes the baroque fountains, adding majesty and charm to the lavish palaces bordering the cobblestones. Vendors fill their stalls with decorations, bright sweets, and traditional Christmas cuisine. The elaborate light display in the Church of Sant’Agnese in Agone accentuates the enchanting, picturesque market. Jugglers and dancers perform alongside the trickling waters of the Fountain of the Four Rivers.

The scent of mozzarella cheese and salami drifts from an artisanal market kiosk. Romans strap on ice skates and swirl around the rink at Parco della Musica. Stalls selling comforting winter foods, such as hot porchetta sandwiches, surround the rink. The serene sounds of a youth choir echo across the square. The splendor of Rome at Christmas welcomes you with open arms, culminating in the unforgettable experience of midnight mass at St. Peter’s Basilica. Michelangelo’s dome crowns the famous church, which adorns the center of St. Peter’s Piazza, framed by pillars. The crisp December air brushes against your cheeks. The square fills with excited Romans equally eager to stand beneath the blessed hands of the pope with a hint of herbaceous frankincense and myrrh filling the air.

What’s Included: breakfast, dinner, tour, accommodation

Day 3: Rome – Dec. 25th – A Holly Jolly Christmas Day

At breakfast, you indulge in a frothy cappuccino as your first gift on Christmas Day. The foam atop the semi-sweet coffee offers a pleasant balance and feisty vigor to begin the day. Meet your guide in the lobby for a splendid exploration of Rome on Christmas Day. Many Romans spend time with family and friends by indulging in a lunch that lasts until the evening. Dishes such as pasta in a savory broth accompany the traditional panettone. Your guide offers cheerful and exuberant commentary while taking you through the iconic walkways of the city.

The Pantheon connects the ancient traditions with Christian heritage. The structure was originally erected as a temple in the 2nd century AD. Pope Boniface IV consecrated the grounds as a Christian Church in the 7th century. The interior niches contain statues lit by the central opening in the dome, the only lights source in the former temple. The symmetry between the height of the dome, standing at 142 feet, and the size of the interior, which has a diameter of 142 feet, adds to the harmonious aesthetic. The splendor of Rome continues long into Christmas Day with lights strung alongside the marble stairway of the Spanish Steps and glowing against the off-white façade of the Trinita dei Monti church overlooking the stairs. In a small, traditional café, your guide orders you a hot chocolate. The luscious, dark chocolate flavor fills you with gratifying warmth in the traditional Roman December air.    

What’s Included: breakfast, dinner, tour, accommodation

Day 4: Florence – Dec. 26th – Markets of the Renaissance

The morning brings memories of the festive atmosphere and charming lights of Piazza Navona’s Christmas Market. The excitement of the families and couples wandering across the cobblestones repeats in your head at breakfast. You sip your fresh espresso and bask in the soothing flavor of the iconic Italian breakfast drink. You have a private transfer to Rome Termini Railway Station. Board the first-class compartment for a relaxing scenic ride over the Lazio countryside and into Tuscany. Once in Florence, your private transfer leads you from Santa Maria Novella Station to a luxurious hotel located in the Renaissance city’s historic center. Christmas may have ended, but the festivities continue.

Colorful lights strung across the cobblestone walkways add flair to the day and night with tracing images of dangling stars, bells, and ribbons. The scent of freshly made waffles emanates from the gelaterias and cafes lining Via de’ Tornabuoni. Large windows of boutique shops and department stores demonstrate elaborate displays. Locals enjoy the cool air by ice-skating on the seasonal rink at Piazza della Liberta. You can join in the fun set amidst the northernmost point of the historic city center, encompassing the Triumphal Arch of the Lorraine, erected to welcome the presence of the Habsburg dynasty in the 18th century. For a cultural view of Florence, you meet your guide and embark on a private tour of the city’s elaborate churches, beginning with the Medici Chapels at San Lorenzo.

What’s Included: breakfast, transfer, tour, accommodation

Day 5: Florence – Dec. 27th – Enchanting Tuscan December

In the morning, the cafes set out tables in the Piazza del Duomo, beneath the breathtaking dome of the Florence Cathedral. The pink, green, and white marble of the façade contains lavish statues embellishing the beauty of the 15th-century structure. After breakfast, you venture south to the Tuscan city of Siena, which once rivaled Florence for Tuscan supremacy. Strong stone walls from the 12th century continue to encircle the historic city center. Cobblestone streets meander between narrow alleyways and open into the magnificent space of Piazza del Campo; Palazzo Pubblico frames the piazza with rustic stone walls and a soaring 14th-century tower standing 367 feet tall.

The complex of Santa Maria della Scala was erected in the 9th century as a hospital accommodating pilgrims en route to Rome. It stands near the remarkable figure of Siena’s cathedral and displays an elaborate collection of artworks providing insight into the history of artistic expression and culture around Siena and Tuscany. The museum contains four floors, with three open to the public. In the Pilgrim’s Hall, you find a cycle of frescoes depicting the history of the hospital as told through the art of several 13th-century artists. The frescoes overtake the walls and vaulted ceilings, connecting the remarkable stories of the hospital with the traditions of pilgrims eager to visit the capital of Christianity at Rome, offering a unique perspective on art, history, and culture during the season of giving.

What’s Included: breakfast, tour, accommodation

Day 6: Florence – Dec. 28th – Themes from the Art World

Although Christmas has come and gone, the cheerful ambiance remains, emanating from the wide smiles of locals and the continuous glow of the lights strung along the streets of Florence morning, noon, and night. You meet your guide after breakfast and walk from the comforts of your centrally located hotel to the gorgeous piazzetta of the Uffizi Gallery. The exterior walls frame the rectangular space with a set of columns offering a view of the banks of the Arno River.

Cosimo I de’Medici funded the project in the 16th century to house the Florence magistrate’s offices. The Medici family supported the arts and beauty of the city to capture the splendor of life and to emphasize their wealth and power over Tuscany. A marble stairway leads to the second story where famous paintings decorate the main galleries. The winter light pours through the large open windows along the halls, glinting off of the gilded frames and marble busts.

The galleries are arranged by period, offering you a chance to compare works of different artists with their contemporaries to see the evolution of artwork in Italy over time, and to contrast the techniques various artists utilized. In the Renaissance Gallery, The Birth of Venus catches your eye. Botticelli painted the piece in the 15th century, depicting the allegory of the Roman goddess of beauty’s beginnings, as birthed from the sea. The master artist humanized the gods of mythology during a time of Christian devotion; he took inspiration from and utilized the mythologies of, the classics.

What’s Included: breakfast, tour, accommodation

Day 7: Florence – Dec. 29th – Into the Christmas Culture of Pisa

In the winter, the Tuscan countryside fills with the aroma of chestnuts. Vendors roast chestnuts in the open squares beneath the lingering lights of Christmas. Today you return to the Tuscan countryside with a full day tour visiting the charming cities of Pisa and Lucca. Pisa is more than the Leaning Tower and the Piazza dei Miracoli. The youthful exuberance from the students at the nearly 700-year-old university contrasts the antique homes and lavish structures spanning the cobblestone streets. The winter aroma of chestnuts blends with the comforting scent of a traditional Tuscan beef stew emanating from a local restaurant.

The holiday season is the perfect time to visit Campo Santo, also referred to as the Sacred Field. According to legend, the rectangular cloister of gothic arches borders Roman sarcophagi and tombs of Pisan patricians set beneath what was once soil taken from Calvary, where Christ was crucified, during the Fourth Crusade. The 14th and 15th-century frescoes lavishly decorate the interior walls beside red-pigment sketches connoting the original details of the artist’s intent. Once at the Leaning Tower of Pisa, you find the 12th-century marble structure fascinating as it lists nearly four degrees. You climb the more than 290 steps to the tower’s top tier for a view of Pisa decorated with an intimate holiday light.

What’s Included: breakfast, tour, accommodation

Day 8: Milan – Dec. 30th – The Lights of Cinque Terre

Today you leave behind the Renaissance palaces and unique history blending classic culture and Christian tradition around Florence’s wondrous streets. Your private transfer escorts you north to the famous city of Milan, the capital of the Lombardy region. You have the option to venture southwest out of Florence to reach the treasured shores of Cinque Terre in the Liguria region. In the summer, the trails crisscrossing the five secluded towns fill with adventurers eager to take in the panoramas of Mediterranean Sea.

In the winter, the five towns have a tranquil ambiance in the cool Mediterranean breeze. The mountain promontories border each town, separating them from one another amidst the Maritime Alps. The refreshing aroma of the sea replaces the scent of roasting chestnuts in Tuscany. The town of Manarola is the second most southerly town of the grouping, set beside the more notable Riomaggiore. The towns remained isolated from the rest of Italy and the world until the mid 19th century when the Italian government built a train connecting Genoa to Rome.

The aroma of Baccala stew emanates from the cellar restaurants in town. Manarola is the oldest of the five towns, proud of its Roman roots, and overlooks the small natural harbor bordered by a sea break. Fishing boats wade in the quiet winter waters. Vineyards overtake the mountain terraces. More than 250 Christmas characters draped in lights create the intimate and dramatic Nativity scene traversing the mountainside along the trail to the hilltop church. The sun sets rather early in the winter, allowing the brilliant light of the Nativity scenes glows against the darkness.

What’s Included: breakfast, transfer, tour, accommodation

Day 9: Milan – Dec. 31st – A Fashionable New Year’s Eve  

Milan contains a poised beauty set against the backdrop of an industrial city famous for being a leader in world-class fashion. The cathedral in the center of the city radiates grace and drama with 135 delicate spires, accented by more than 2,200 marble statues. The large stained glass windows in the nave offer brilliant natural light embellished with captivating color. The day is at your leisure to wander the canals of the city, which remains a favorite pastime for locals, or witness the exemplary artwork inside the church of Santa Maria delle Grazie, which displays Leonardo da Vinci’s Last Supper.

The city pulses with the energy of locals both young and old, happy to celebrate the coming year with friends, family, and foreign visitors. Cafes set your heat lamps around their outdoor tables. Patrons dine on steaming plates of rich risotto and watch passersby stroll alongside Navigli canal. Visit the La Scala Museum for an introduction to the history of the world-famous opera house. The gorgeous center for the musical arts often fills with opera enthusiasts from around the Lombardy region.

The museum was established in the early 20th century and focuses on the history of opera and the opera house, as told through a series of collected costumes, paintings, set designs, and scores. The theater comes to life in the detailed costumes telling tales of woe and wonder both on and off the stage. After a lavish three-course dinner, you enter La Scala and are immediately attracted to the crescent design overlooking the stage. Your private box offers a perfect view to the Coppelia Ballet. 

What’s Included: breakfast, dinner, tour, accommodation

Day 10: Milan – Jan. 1st – A New Year’s View of Italy

The lights and color shows of New Year’s Eve have faded to a quiet January first morning. The scent of freshly baked brioche is faint but continues to drift along the streets for a sweet aroma to begin the New Year. Even the industrious city of Milan wakes late today, providing locals who have remained in the city to celebrate a chance to relax. You have grown accustomed to enjoying the rich flavor of a fresh espresso at breakfast. You offset the slightly bitter taste of the strong brew with a bite of a sweet-crusted brioche. After breakfast, your private transfer meets you at the hotel and escorts you to Milan Malpensa International Airport for your flight home. You could always extend your stay and venture to the mountains to hit the snow-blanketed Dolomite slopes, or travel south to enjoy the warm sands of Sicily.  

What’s Included: breakfast, transfer 


Starting Price 

This trip is customizable for your private travel.

What's Included 

  • Accommodations
  • In-country transportation
  • Some or all guided tours and activities (dependent on season)
  • Expert trip planning
  • 24x7 support during your trip
The starting price is based on travel during the low season for a minimum of two travelers staying in shared 3-star accommodations. Please inquire for a custom trip quote based on your travel preferences and travel dates.