Christmas in Tuscany 8-day tour
Florence (1 night), Siena (4 nights), Montepulciano (2 nights)
This is a sample itinerary which is completely customizable, ask us how.
Highlights of the trip
- Florence and Siena Christmas markets and exploration
- Visit medieval fortress village of San Gimignano
- Thermal bathing experience in Terme di Montecatini
- Stay in Montepulciano and sample famous local wine
- Nature hike or skiing at Monte Amiata near Val d'Orcia
- Guided tours of Lucca and Pisa with the leaning tower
Daily Itinerary
Day 1: Arrival in Florence
Arrive in Florence, check into your hotel, and explore the city adorned with festive Christmas lights. Visit the Christmas market in Piazza Santa Croce, famous for its German-inspired stalls offering mulled wine, artisanal crafts, and holiday treats. End the day with a Florentine holiday dinner and a stroll across the illuminated Ponte Vecchio.
Overnight: Florence
Day 2: Thermal baths - Terme di Montecini
After breakfast our driver will pick you up and take you to Terme Montecatini known for its healing thermal waters and Art Nouvou architecture. Spend a relaxing day in the baths, with options for luxurious spa treatments while admiring the elegant architecture.
Overnight: Florence
Day 3: Siena - medieval charm
Travel to Siena and immerse yourself in the Christmas spirit at the Piazza del Campo Christmas market. Wander through Siena’s medieval streets, visit the Siena Cathedral, and enjoy a Sienese dinner with local dishes like wild boar pasta.
Overnight: Siena
Day 4: San Gimignano with wine tasting
Private guided excursion to San Gimignano, where you’ll explore the medieval town’s Christmas market and learn about the significance of famous medieval monuments such as Torre Grossa, Piazza della Cisterna, and the Collegiate Church of San Gimignano.
Enjoy a typical Tuscan lunch paired with local wine before heading back to Siena.
Overnight: San Gimignano
Day 5: Montepulciano - Christmas village
Head to Montepulciano, where the town transforms into a Christmas wonderland with a market and Santa’s village at the castle. Spend the day browsing the stalls, ice skating, or enjoying the festive activities, then relax at a local agriturismo with a Tuscan dinner and local wines.
Overnight: Montepulciano
Day 6: Day trip to Monte Amiata
Private excursion to Monte Amiata, a unique volcanic ski area near the Val d’Orcia. The slopes are easy for beginners and a perfect day trip for the family or anyone who loves nature.
If the conditions are not snowy, it is the perfect spot for a nature hike with panoramic views of the surrounding Tuscan countryside.
Continue to Pienza near Val dOrcia for the night.
Overnight: Montepulciano
Day 7: Pienza and Val d’Orcia
Explore the beautiful town of Pienza in the morning, known for its architecture and local cheeses. In the afternoon, take a scenic drive through the Val d’Orcia, stopping in Montalcino for a wine tasting. Return to your agriturismo for a Christmas-themed dinner featuring local ingredients.
Overnight: Pienza
Day 8: Day trip to Cortona
Private transfer to Lucca, where you’ll walk along the city’s medieval walls and visit the Christmas market in Piazza Napoleone. Spend the evening attending a holiday concert in one of Lucca’s historic churches or theaters, enjoying festive music in the charming setting.
Overnight: Montepulciano
Day 9: Pisa and the leaning tower
A Festive Farewell
Travel to Pisa, with a guided tour of the Leaning Tower and Piazza dei Miracoli. Visit the Christmas market in Piazza Vittorio Emanuele II. Enjoy some last-minute shopping and holiday treats before departing from Pisa or returning to Florence for your flight home.
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