Our Favorite Italy Winter Itinerary with Kids

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Traveling with kids can be an adventure in itself, but when you plan a winter trip to Italy, it becomes a magical experience. We embarked on an unforgettable journey from JFK Airport to Milan on Christmas night with our six-year-old son, Eli. Our 11-day itinerary was packed with exciting activities and delicious food that both parents and kids could enjoy. In this blog post, we'll take you through our favorite winter itinerary in Italy with kids, highlighting each day's activities, meals, and memorable moments.

Day 1: Arriving in Milan

After a long flight, we finally arrived in Milan, checked into our hotel, and started our Italian adventure. The city was beautifully adorned with Christmas decorations, and we headed straight to the Christmas Market (Mercatini di Natale) in Duomo. The festive atmosphere, twinkling lights, and charming stalls filled with local crafts were a perfect introduction to Italy during the holiday season. For dinner, we had an incredible meal at Giacomo Arengario, a restaurant that offered a breathtaking view of the iconic Duomo.

Day 2: Exploring Milan

Our second day in Milan began with a hearty breakfast at our hotel. Afterward, we embarked on a self-guided tour of the magnificent Duomo. Climbing to the roof and exploring the church's interior left us in awe of its beauty and history. For lunch, we tried something different at Hana, a Korean restaurant where Eli enjoyed some familiar flavors. The Milan Natural History Museum was our next stop, where we marveled at the exhibits and learned about the world's biodiversity (read more about our visit to the museum here). As we strolled to dinner, we stumbled upon a massive Christmas village (villaggio delle meraviglie) filled with thrilling rides and festive decorations, offering unexpected joy and laughter.

Day 3: More Milan Adventures

On our third day in Milan, we decided to take it easy in the morning and enjoyed a leisurely breakfast at the hotel. Our next stop was the Leonardo da Vinci Museum of Science and Technology, a fascinating experience for both kids and adults. The highlight of the day was undoubtedly our visit to see Leonardo da Vinci's masterpiece, the Last Supper. It exceeded our expectations and left us in awe of the artist's genius (read more about our experience here).

Off to Florence!

Day 4: Journey to Florence

After a bit of shopping in Galleria Vittorio, we bid farewell to Milan and boarded a train to Florence. Arriving in Florence, we checked into our hotel and enjoyed a leisurely walk, soaking in the city's holiday lights. Dinner at Il Latini was a memorable culinary experience, topped off with the best tiramisu we've ever had.

Day 5: Florence's Artistic Treasures

Our first morning in Florence was dedicated to the Uffizi Gallery, where we had pre-booked tickets to avoid long lines. For lunch, we savored delicious Italian cuisine at Osteria Vini e Vecchi Sapori, a culinary highlight of our trip. In the afternoon, we had a family photoshoot session to capture beautiful memories of our time in Florence (read about our experience here). Dinner at Trattoria Dall'Oste was another gastronomic delight.

Day 6: Pisa and Art Adventures

A short train ride took us to Pisa, where Eli's excitement to see the iconic Leaning Tower of Pisa was palpable. Although he couldn't climb it (the minimum age is 8), we had a blast taking pictures and enjoying delicious pizza nearby. Upon returning to Florence, we visited the Galleria dell'Accademia to see Michelangelo's David, an awe-inspiring masterpiece.

Day 7: Arrival in Rome

We checked out of our Florence hotel and hopped on a train to our final destination: Rome. Upon arrival, we ventured into the city center for sightseeing but decided to retreat to our hotel due to the New Year's Day parade's bustling crowds.

Day 8: Roman Adventures

A light breakfast was followed by a relaxing morning, and we couldn't resist trying out McDonald's in Italy for lunch. In the afternoon, we explored the Colosseum and the Palatine Hill, which left Eli and us in absolute awe.

Day 9: Exploring Rome's Iconic Sights

Our morning began with a cab ride to the city center to visit the Trevi Fountain, where Eli made wishes by throwing two coins into the water. We continued our exploration with stops at the Spanish Steps, the Pantheon, and Piazza Navona, where Eli enjoyed a carousel ride. After a leisurely lunch and some shopping, we visited the Vatican Museum early evening.

Day 10: A Day of Leisure in Rome

On our penultimate day, we indulged in a leisurely day of walking, shopping for souvenirs, and enjoying the beauty of Rome. Eli's favorite spot, Piazza Navona, was revisited for another carousel ride, and the Christmas Market added a festive touch. In the early evening, we concluded our Italian adventure with a pasta making class, learning the art of making pasta the Italian way.

Day 11: Heading Home

With heavy hearts, we made our way to FCO Airport to catch our flight back home, carrying with us cherished memories of our winter adventure in Italy.

Bottom Line

Our Italy winter itinerary with kids was an extraordinary experience filled with cultural discoveries, delicious food, and memorable family moments. From Milan's enchanting Christmas markets to Florence's artistic treasures and Rome's iconic sights, this journey offered a perfect blend of adventure and relaxation. Traveling with kids can be a joy when you plan a well-rounded itinerary that caters to both young and adult interests, creating a trip filled with cherished memories that will last a lifetime. Italy's winter charm added an extra layer of enchantment to our family adventure, and we hope that our itinerary inspires you to plan your own unforgettable winter getaway with your loved ones.

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Milan Natural History Museum