Our professional driver will pick you up directly from your hotel, B&B, or private apartment and take you on a scenic drive through the rolling hills between Umbria and Tuscany. Along the way, we’ll pass near the beautiful Trasimeno Lake — a stop can be arranged upon request. Surrounded by lush greenery, reeds, and graceful white water lilies, Trasimeno Lake is a true natural paradise, home to wild ducks, cormorants, kites, and kingfishers — the perfect spot to enjoy a peaceful break and stunning views.

First Stop: Cortona – Free Visit Discover Cortona, the main cultural and artistic center of the Val di Chiana after Arezzo. Founded by the Etruscans (original name Curtun), the town still preserves impressive remains from its ancient past. Cortona boasts a rich artistic heritage, with connections to great Renaissance masters such as Luca Signorelli and Beato Angelico, as well as Pietro da Cortona from the Baroque period. Before your self-guided walking tour, your English-speaking driver will provide you with the main directions and tips to help you explore the town at your own pace. The charming streets, panoramic views, and timeless atmosphere of Cortona also inspired the famous movie “Under the Tuscan Sun.” Just outside the town, you’ll visit the peaceful Hermitage of San Francesco – Le Celle, a spiritual retreat surrounded by nature and history.

Second Stop: Montepulciano – Free Visit and Wine Tasting Enjoy a stop in Montepulciano, a beautiful medieval hilltop town famous for its wines and authentic Tuscan charm. Known for its pork, pecorino cheese, handmade “pici” pasta, lentils, and honey, Montepulciano is celebrated worldwide for Vino Nobile di Montepulciano DOCG and Rosso di Montepulciano. Your English-speaking driver will accompany you to the historic wineries, providing directions and tips for a self-guided walking tour of the town. In the ancient underground cellars, a qualified winemaker will show you the impressive oak barrels where the famous wines are aged. After the visit, enjoy a guided wine tasting of the estate’s top wines, with insights into their unique characteristics. If you wish, your driver will recommend great local restaurants for a traditional Tuscan lunch. At the end of your visit, we will depart from Montepulciano and head to Florence, arriving after about 1 hour and 30 minutes of scenic driving.