Day 1 – Morning: Christmas Magic in Montepulciano
- Discover the Christmas Markets of Montepulciano Begin your Christmas journey in Montepulciano, one of Tuscany’s most beautiful Renaissance towns, famous for its historic architecture, charming streets and world-renowned Vino Nobile wine.During the Christmas season, the town transforms into a magical festive destination, with traditional wooden market stalls decorating Piazza Grande and the surrounding streets. Explore the Montepulciano Christmas Market, where you can discover handcrafted gifts, Christmas decorations, traditional sweets and local Tuscan specialties. The magnificent Renaissance buildings create a spectacular backdrop for this unforgettable holiday experience.
- Visit Santa Claus’s Castle Continue your visit with one of Montepulciano’s most beloved Christmas attractions: Santa Claus’s Castle, located within the town’s historic fortress.This enchanting Christmas experience is particularly popular with families, offering festive decorations, themed activities and opportunities for children to discover the magical world of Santa Claus. Before leaving Montepulciano, enjoy the beautiful panoramic views of the Tuscan countryside and take some time to taste traditional local products.
Day 1 – Early Afternoon: Christmas in the Medieval Town of Cortona
- Explore Cortona’s Historic Center Continue your Christmas adventure to Cortona, an ancient Etruscan town overlooking the beautiful Valdichiana Valley.Begin your visit in Piazza della Repubblica, the heart of Cortona’s historic center, where the impressive Palazzo Comunale and its monumental staircase create one of the town’s most recognizable scenes. Walk towards Piazza Signorelli, surrounded by elegant historic buildings, traditional shops and charming medieval streets. During the Christmas season, festive decorations and local celebrations add a special atmosphere to this beautiful Tuscan hilltop town.
- Discover Cortona’s Christmas Atmosphere and Panoramic Views Take a leisurely walk through Cortona’s picturesque cobblestone streets, discovering artisan boutiques, traditional architecture and beautiful viewpoints overlooking the surrounding countryside.Depending on the dates of your visit, you may encounter Christmas events, seasonal exhibitions, festive installations and local entertainment organized throughout the historic center. Before continuing your journey, stop at one of Cortona’s panoramic terraces to admire the breathtaking views of the Valdichiana and Lake Trasimeno in the distance.
Day 1 – Late Afternoon and Evening: Christmas Lights on Lake Trasimeno
- Explore the Medieval Village of Castiglione del Lago Travel to Castiglione del Lago, a picturesque medieval town overlooking Lake Trasimeno, just across the border between Tuscany and Umbria.Discover its charming historic center, traditional stone streets and the impressive Rocca del Leone, a medieval fortress offering spectacular views of the lake and surrounding countryside. The peaceful lakeside atmosphere and beautiful historic architecture make Castiglione del Lago a wonderful destination during the winter season.
- Experience the Magic of Luci sul Trasimeno As evening approaches, discover the magical atmosphere of Luci sul Trasimeno, when this celebrated Christmas event is scheduled.The event is particularly famous for its spectacular illuminated Christmas tree installation on Lake Trasimeno, creating an extraordinary display of festive lights reflected across the water. Depending on the annual Christmas program, visitors may also enjoy traditional markets, illuminated decorations, family attractions and festive entertainment. End your first day surrounded by the enchanting reflections of Christmas lights on the lake, one of the most memorable holiday experiences in Umbria.
Day 2 – Morning: Discovering Arezzo, the City of Christmas
- Explore Piazza Grande and Arezzo’s Historic Center Begin your second day in Arezzo, one of Tuscany’s most fascinating historic cities and a spectacular destination during the Christmas season.Start your visit in Piazza Grande, the magnificent medieval square surrounded by historic palaces, elegant loggias and remarkable architecture. This beautiful square becomes the heart of Arezzo Città del Natale, one of Tuscany’s best-known Christmas celebrations. Explore the surrounding streets, discover traditional shops and admire the architectural treasures that make Arezzo such a remarkable destination.
- Visit the Tyrolean Christmas Village Discover the famous Tyrolean Christmas Village, traditionally hosted in Piazza Grande during the festive season.Inspired by Alpine Christmas traditions, the market features charming wooden chalets offering handmade gifts, Christmas ornaments, artisanal products and seasonal specialties. Enjoy the aromas of roasted chestnuts, festive sweets and traditional winter drinks while exploring one of the most atmospheric Christmas markets in Tuscany. The combination of medieval Tuscan architecture and Alpine Christmas traditions creates a truly unique holiday experience.
Day 2 – Afternoon: Christmas Attractions and Tuscan Traditions
- Discover Arezzo’s Christmas Attractions Continue exploring the magical atmosphere of Arezzo Città del Natale, where festive decorations, seasonal attractions and Christmas entertainment bring the historic center to life.Depending on the official event calendar, visitors may discover Santa Claus-themed attractions, Christmas installations, family activities and festive performances throughout the city. Take time to explore Arezzo’s charming streets, admire its historic buildings and enjoy the lively atmosphere of the Christmas season.
- Taste Traditional Tuscan Christmas Specialties A Christmas tour through Tuscany would not be complete without discovering the region’s authentic culinary traditions.Enjoy a traditional Tuscan lunch or explore the seasonal food stalls offering roasted chestnuts, artisanal sweets, hot chocolate, mulled wine and other Christmas specialties, depending on availability. Arezzo is also home to traditional restaurants and local establishments where you can experience the genuine flavors of Tuscan cuisine. This is the perfect opportunity to relax, enjoy the festive atmosphere and discover another delicious side of Christmas in Italy.
Day 2 – Late Afternoon and Evening: The Magic of Christmas Lights in Arezzo
- Admire Arezzo’s Christmas Lights and Illuminated Squares As the sun begins to set, discover another enchanting side of Arezzo, when Christmas lights illuminate its historic streets and beautiful squares.During scheduled events, festive light projections and artistic installations transform the city’s architecture into a spectacular Christmas setting. Return to Piazza Grande to admire its magical evening atmosphere, explore the illuminated Christmas market when open and capture unforgettable photographs of this beautiful Tuscan city.
- End Your Christmas Journey with Unforgettable Memories Conclude your two-day Christmas adventure with a final stroll through Arezzo’s beautifully decorated historic center.From the Renaissance elegance of Montepulciano to the medieval charm of Cortona, from the spectacular Christmas lights of Lake Trasimeno to the festive atmosphere of Arezzo, this journey offers an unforgettable introduction to Christmas in Tuscany and Umbria. Experience the magic of Italian holiday traditions, discover beautiful historic towns and create wonderful memories surrounded by the lights, colors and authentic spirit of Christmas.
- Best time to visit: Late November through early January is generally the main Christmas season. Individual attractions and Christmas markets may operate on selected dates.
- Wear comfortable shoes: The historic centers of Montepulciano, Cortona and Arezzo feature cobblestone streets, steps and uphill sections.
- Dress warmly: Winter temperatures can be cold, especially during evening visits to Christmas markets and illuminated attractions.
- Bring a camera: Capture the festive markets, medieval streets, panoramic landscapes and spectacular Christmas lights.
- Christmas market schedules: Check official opening dates, as some markets and attractions operate mainly on weekends and public holidays.
- Transportation: A private vehicle is recommended for comfortable travel between the four destinations.
- Accommodation: An overnight stay in the Valdichiana area provides a convenient base for exploring Tuscany and Umbria.
- Families with children: Montepulciano and Arezzo offer popular family-friendly Christmas experiences, subject to seasonal schedules and availability.
- Twin share or double accommodation, all breakfasts and three evening meals per week, Italian style.
- Three all day excursions of your choice during each week.
- Local excursions for local markets or shopping, and to nearby sites for painting, walking and exploring.
- All local transport included and transfers to and from the railway station.
Cancellation Fees:
The initial deposit (per person) from date of confirmation up to the start of your stay with us. Dates for booking: Saturday to Saturday.