14-Day Italian Christmas Itinerary: Winter Beauty and Festive Traditions

Rome is a beautiful mixture of contemporary life and haunting ruins brought into intense focus during the Christmas season. With romantic lights dangling over the cobblestone streets and hints of the ancient world emerging around every corner, the city’s undeniable charisma will welcome you upon your arrival. Your private transfer will escort you into the heart of the city, where you will have the day at your leisure. With much more to enjoy, you can spend your time in the Christmas Market in Piazza Navona, where spiced aromas meet the lively ambiance interspersed with vintage collections and holiday decor.

The splendor of Imperial Rome will emerge during your guided tour. After exploring the marvels of the Colosseum, your private guide will take you through the Roman Forum, which represents the heart of the former empire’s civil and religious life. You can wander along two millennia of history featured in the remains of the Temple of Antoninus Pius and the Arch of Septimus.

You can continue to the mountain town of Tivoli to visit Hadrian’s Villa, the impressive ruins of the former emperor’s palace spanning over 296 acres. Sculptures reflect in the waters of rippling in the 393-foot long pool. After exploring Imperial Rome, you can enjoy the remainder of the day in the cozy lights and holiday ambiance spreading through the city as the aromas of candied oranges and cinnamon fill the neighborhood bakeries.

The wonders of Classic Rome will open up to the city's iconic images as your guide leads you to monuments like the Trevi Fountain and Spanish Steps. The marbled stairway connects Piazza de Spagna to the French church of Trinita dei Monti. After discovering the quintessential piazzas of Campo dei Fiori and Piazza Navona, you can continue to the Vatican to explore St. Peter’s Basilica and the museum galleries. The School of Athens painting reflects how master artist Raphael constructed symmetry and cultural analogy before enter the Sistine Chapel to view the embodiment of the Renaissance.

After breakfast, you may head to Rome’s catacombs that once edged the city’s center nearly two millennia ago. The early Christian catacombs will take you underground into a labyrinth of burial grounds dating back to the 5th century. The iconography on the walls features early symbols such as the ichthys leading to the original burial places of saints like St. Cecilia. In the evening, you can return to the Vatican for a completely different experience that celebrates the holiday spirit, ancient tradition, and contemporary connections to Christmas as you celebrate the season with Mass at St. Peter’s Basilica.

On Christmas, the aromas of spiced orange and lemon drift from the panettone cakes on display in bakeries across the city. Ice skating rinks bring a touch of the winter ambiance to corners of the city including beneath the dramatic facade of the Castel Sant’Angelo. You can indulge in Christmas with a traditional lunch at a favorite restaurant to find roast lamb, stracciatella soup, and cannelloni. Church concerts may also keep the festive ambiance ringing across the cityscape. The Church of Santa Maria in Aracoeli displays the statue of Santo Bambino carved from a single piece of olive wood.

The Christmas spirit continues after the holiday ends with the festive ambiance lasting until January. The aromas of mulled wine or pan d’oro may still fill the city throughout the day as you explore Rome and its surroundings at your preferred pace. You can travel into the hidden layers of the city with an underground tour to uncover Roman houses or find more insight into the ancient strength of the city with a visit to Ostia Antica.

The city's distinctive culture can come to the forefront with a Christian Rome excursion that can take you to the most distinctive churches in the city, including the Basilica of Saints Quattro Coronati and Sylvester Chapel, where the 13th-century medieval frescoes drape across the cloister walls.

After traveling to Venice in the morning, you can discover the glamour of the imperial city on an iconic gondola ride along the narrow canals. The perspective of the marble palaces and bustling neighborhoods may shift as you find the quiet corners of the city away from the bulbous domes of St. Mark’s Basilica and the columns of the Doge’s Palace. Venice during the holiday season shimmers with strung lights, elegant masks, and shimmering glass. You can continue uncovering the unique beauty of Venice with a private tour of the famous islands reaching Murano, Burano, and Torcello. Dazzling glasswares may decorate shop walls as artisans continue to craft in their workshops.

With so many ways to discover the wonders of Venice, you could tour the highlights to find the gilded mosaics of St. Mark’s Basilica or explore the cuisine with a cicchetti tour sampling the typical and traditional flavors of the city. A Prosecco tour will help you celebrate the holiday season with a different combination of flavors as your guide takes you out of the city and into the countryside to visit the abbey of San Pietro di Feletto.

13th- and 14th-century frescoes decorate the Romanesque interior and eventually lead you along the ancient road winding through the Alps. You will reach a vineyard uncovering the secrets of Valdobbiadene to find a prosecco with floral and fruity aromas that embody the essence of Christmas.

You will travel to Tuscany in the morning to find the essential splendor of rolling hills, cypress trees, and preserved towns. Before settling into the wonders of Siena inside the dramatic medieval walls, you can stop in the town of Lucca, which is known for its preserved ramparts and crowning central tower. Holm oak trees grow at the top and remain visible from around the historic center. In Pisa, you can explore the Piazza dei Miracoli. The marble design of the cathedral highlights the prestige of the former city-state while guiding you to the famous Leaning Tower.

The architecture climbs high and lofty in Siena as the historic streets act like an open-air museum. The shops will continue to display Christmas trinkets and decorations carrying on the tradition of celebration into January with the Feast of the Epiphany. Lights, aromatic herbs, and the scent of comforting winter deserts like the chestnut-based cake castagnaccio may drift through the streets.

With the day at your leisure to enjoy the city’s beauty and the charms of the surrounding Tuscan countryside, you could wander the art collections and the formidable design of the cathedral dusted with the sweet aromas of neighboring pastry shops, or venture into the landscape with a guided truffle hunt. A truffle hunt will introduce you to Tuscany’s lush forests. Your guide may give you a history of truffles in Italian cuisine as you search the undergrowth following a specially trained dog.

Your private transfer will greet you at the hotel lobby after breakfast and can escort you into the heart of Florence after first touring the greater splendor of Tuscany. You can spend time sampling the dynamic flavors of the region with a tour of the medieval hilltop towns and notable vineyards scattered across the hills. In San Gimignano, you may view the 14 towers soaring above the hills. The history feels tangible as you stroll the cobbled lanes and enjoy the panoramas across the countryside. You can visit a local vineyard to taste the citrusy notes of local Vernaccia wine.

As the city continues celebrating the Christmas season, many Florentines get ready for the grand Feat of the Ephiphany Parad. Magnificent costumes evoke a sense of the Three Wise Men while the typical Tuscan soup of ribollita creates a comfortable ambiance in the neighborhood restaurants.

With the day at your leisure to delight in Florence’s history and heritage, you could visit the Boboli Gardens to view the manicured Italianate design or spend time in the galleries of the Old Palace. For an invitation into the heart of the Renaissance, you could take a guided tour of the Uffizi Gallery and the halls dating back to the 16th century. As the timeline unfolds showing the evolution of art in Italy, you may find jewels of the Enlightenment with displayed works by Michelangelo and da Vinci, as well as Botticelli’s work, including La Primavera.

The day is once more yours to fill with exploration and discovery at your pace. From entering into the Accademia to find Michelangelo’s David to touring the flavors of Tuscany with a private cooking class, you can find the spirit of the season and the soul of the region. You can sample the tastes of the city with a guided food tour that could take you from the Central Market where vendors offer samples of local cheese and meats to a historic gelateria that features the delicate touches of winter in flavors like hazelnut or cinnamon.

You can spend your final morning in Florence as you prefer, from enjoying a cappuccino and brioche at a popular cafe to taking in the morning panoramic view from Piazzale Michelangelo. If you have time, you can also visit the Medici tombs in San Lorenzo Church before your private transfer escorts you to the train station for the fast train to Rome, where you will reach the airport with plenty of time to check-in for your flight home.