Our professional driver and expert tour leader will pick you up directly from your hotel, B&B, or private apartment, ensuring a comfortable and seamless start to your private tour of the Tuscan countryside. The journey begins with a scenic drive through rolling hills, vineyards, and olive groves before reaching Cortona, one of the most charming and historic hill towns in Tuscany. Perched at 600 meters above sea level, Cortona boasts spectacular panoramic views over the Valdichiana valley and Lake Trasimeno. During your self-guided visit, you can discover: • Piazza della Repubblica, the historic heart of Cortona • The picturesque medieval streets of the old town • Piazza Signorelli, home to cultural landmarks • Local artisan shops and boutiques, perfect for unique souvenirs The tour also includes a visit to the Monastery of St. Francis, a peaceful and spiritual retreat just outside the city center, surrounded by nature and offering a moment of quiet reflection.

After our visit to Cortona, we will stop along the iconic scenic road made famous by the movie “Under the Tuscan Sun”, a perfect spot for memorable photos immersed in the rolling Tuscan landscape. Our journey then continues to Montepulciano, one of Tuscany’s most celebrated hill towns, renowned worldwide for its historic wine cellars and Vino Nobile di Montepulciano DOCG. Here, you will discover the fascinating “Underground Wonders of Montepulciano”, an extraordinary network of ancient tunnels and cellars carved beneath the city. The visit includes: • Piazza Grande, the elegant main square and cultural heart of Montepulciano • The historic Government Palace • Two ancient underground wine cellars, located beneath Renaissance palaces Inside these remarkable cellars, you will admire massive oak barrels used to age the prestigious Vino Nobile di Montepulciano DOCG and Rosso di Montepulciano DOC, offering an authentic insight into the centuries-old Tuscan winemaking tradition.

After exploring Montepulciano, you will enjoy a first wine tasting at Cantina Talosa, where you can sample some of the region’s finest wines and learn about the local winemaking traditions. Next, you will take a guided tour of Montepulciano’s historic underground cellars, known as the “Underground Wonders” (Meraviglie Sotterranee), exploring ancient tunnels and wine-aging spaces that showcase centuries of Tuscan winemaking heritage. Following this immersive experience, you will savor a traditional Tuscan lunch served inside Cantina Ercolani, prepared with seasonal ingredients and local specialties. During the meal, a carefully curated wine tasting of 7–8 local wines, including Vino Nobile di Montepulciano DOCG and Rosso di Montepulciano DOC, will accompany each dish, offering a perfect pairing of Tuscan cuisine and regional wines. This experience provides an authentic and relaxing culinary journey in the heart of Montepulciano’s wine heritage.