Embark on an exclusive private tour from Florence and explore the enchanting medieval Tuscan hill towns of Cortona and Montepulciano. Marvel at their beauty, visit iconic film locations, and indulge in the world-famous Vino Nobile wine.
Embark on an exclusive private tour from Florence and explore the enchanting medieval Tuscan hill towns of Cortona and Montepulciano. Marvel at their beauty, visit iconic film locations, and indulge in the world-famous Vino Nobile wine.
- Duomo di Cortona - Meet the English-speaking driver at the hotel in a comfortable Mercedes-Benz to begin the journey to the stunning Cortona. This town, surrounded by stone walls from Etruscan and Roman times, is perched on a hill approximately 600 meters (about 1968 feet) above sea level. Its elevated position offers breathtaking views of the…
- Duomo di Cortona - Meet the English-speaking driver at the hotel in a comfortable Mercedes-Benz to begin the journey to the stunning Cortona. This town, surrounded by stone walls from Etruscan and Roman times, is perched on a hill approximately 600 meters (about 1968 feet) above sea level. Its elevated position offers breathtaking views of the surrounding valley and Lake Trasimeno. Cortona has gained popularity over the past decade due to Frances Mayes’ book, “Under the Tuscan Sun,” and the movie starring Diane Lane, which is set in Cortona. The protagonist quickly falls in love with the town, its people, and the villa Bramasole, which she buys and renovates. There will be time to relax or explore the area, and the driver will recommend the best activities.
- Piazza Grande a Montepulciano - Depart at 11:30 am for a delightful light lunch at a family-owned winery. Then, continue to Montepulciano with a relaxing 30-minute drive through hills surrounded by breathtaking landscapes. The driver can stop the car anytime for photo opportunities. Arrive in the enchanting Montepulciano around 2 pm. This medieval hill town is of rare beauty, filled with elegant Renaissance palaces, ancient churches, charming squares, and hidden corners. Montepulciano gained significant attention after the filming of the “Twilight” saga sequel “New Moon” and has seen a notable increase in visitors. Walking through Montepulciano is the best way to appreciate the town and its beautiful landmarks, as well as enjoy stunning views of the surrounding countryside, covered with vineyards producing the famous Nobile wine, which can be tasted in the many wine shops within the city walls.

- Hotel pickup and drop-off
- Private tour
- Professional driver/guide
- Transport via Mercedes-Benz V Class with AC
- All taxes, tolls, and parking fees included
- Onboard WiFi access
- Hotel pickup and drop-off
- Private tour
- Professional driver/guide
- Transport via Mercedes-Benz V Class with AC
- All taxes, tolls, and parking fees included
- Onboard WiFi access
- lunch
- Gratuities
- lunch
- Gratuities
Embark on an exclusive private tour through the picturesque Tuscan countryside, where golden fields, olive groves, and cypress-lined roads guide you to two of the region’s most captivating medieval hill towns. In Cortona, a place of timeless allure and renowned from the film Under the Tuscan Sun, explore the narrow stone streets and enjoy panoramic…
Embark on an exclusive private tour through the picturesque Tuscan countryside, where golden fields, olive groves, and cypress-lined roads guide you to two of the region’s most captivating medieval hill towns. In Cortona, a place of timeless allure and renowned from the film Under the Tuscan Sun, explore the narrow stone streets and enjoy panoramic views that extend endlessly across the valley. The adventure continues to Montepulciano, majestically situated on a ridge, where every turn reveals breathtaking vistas over the Val d’Orcia and Val di Chiana — a perfect blend of Tuscany’s beauty and history.
- FOR WINE LOVERS: IS POSSIBLE TO ADD ON THIS TOUR THE VISIT OF A TOP RATED WINERY. PLEASE ADVISE AT THE TIME OF THE BOOKING
- Dress code is casual
- Comfortable shoes
For a full refund, cancel at least 24 hours before the scheduled departure time.
For a full refund, cancel at least 24 hours before the scheduled departure time.