Embark on a private transfer tour from Assisi to Florence and discover the hidden gems of Cortona and Montepulciano. Explore the enchanting landscapes, taste delicious wines, and enjoy the expertise of our driver. Book now!
Embark on a private transfer tour from Assisi to Florence and discover the hidden gems of Cortona and Montepulciano. Explore the enchanting landscapes, taste delicious wines, and enjoy the expertise of our driver. Book now!
- Lake Trasimeno - A professional driver will collect guests directly from their hotel, B&B, or private apartment for a picturesque journey through the rolling hills between Umbria and Tuscany. En route, there is an opportunity to pass by the stunning Trasimeno Lake, with a stop available upon request. Encircled by lush greenery, reeds, and elegant…
- Lake Trasimeno - A professional driver will collect guests directly from their hotel, B&B, or private apartment for a picturesque journey through the rolling hills between Umbria and Tuscany. En route, there is an opportunity to pass by the stunning Trasimeno Lake, with a stop available upon request. Encircled by lush greenery, reeds, and elegant white water lilies, Trasimeno Lake is a true natural haven, home to wild ducks, cormorants, kites, and kingfishers — an ideal location for a tranquil break and breathtaking views.
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Cortona - First Stop: Cortona – Free Visit
Explore Cortona, the primary cultural and artistic hub of the Val di Chiana after Arezzo. Established by the Etruscans (originally named Curtun), the town still retains remarkable remnants from its ancient history. Cortona is rich in artistic heritage, with ties to renowned Renaissance masters like Luca Signorelli and Beato Angelico, as well as Pietro da Cortona from the Baroque era.
Before embarking on a self-guided walking tour, an English-speaking driver will offer key directions and tips to help guests explore the town at their leisure.
The enchanting streets, panoramic vistas, and timeless ambiance of Cortona also served as inspiration for the famous film “Under the Tuscan Sun.” Just outside the town, visitors can explore the serene Hermitage of San Francesco – Le Celle, a spiritual retreat steeped in nature and history.
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Montepulciano - Second Stop: Montepulciano – Free Visit and Wine Tasting
Relish a visit to Montepulciano, a charming medieval hilltop town renowned for its wines and genuine Tuscan allure. Famous for its pork, pecorino cheese, handmade “pici” pasta, lentils, and honey, Montepulciano is celebrated globally for Vino Nobile di Montepulciano DOCG and Rosso di Montepulciano.
An English-speaking driver will guide guests to the historic wineries, providing directions and tips for a self-guided walking tour of the town. In the ancient underground cellars, a skilled winemaker will showcase the impressive oak barrels where the renowned wines are aged.
After the tour, enjoy a guided wine tasting of the estate’s finest wines, with insights into their distinct characteristics.
If desired, the driver will recommend excellent local restaurants for a traditional Tuscan lunch.
Upon concluding the visit, the journey will continue from Montepulciano to Florence, arriving after approximately 1 hour and 30 minutes of scenic driving.

- Bottled water
- Local expert driver and tour leader
- Alcoholic beverages
- In-vehicle air conditioning
- Bottled water
- Local expert driver and tour leader
- Alcoholic beverages
- In-vehicle air conditioning
- Lunch
- Everything not found under the heading inclusions is excluded
- Lunch
- Everything not found under the heading inclusions is excluded
Discover the captivating cities of Cortona and Montepulciano on your journey from Assisi (or Perugia) to Florence with our skilled driver, and unveil the hidden treasures of Tuscany! Enjoy a full-day excursion through the iconic scenery of rolling hills, cypress-lined roads, and medieval hilltop towns, while savoring exquisite wines.
Our service includes…
Discover the captivating cities of Cortona and Montepulciano on your journey from Assisi (or Perugia) to Florence with our skilled driver, and unveil the hidden treasures of Tuscany! Enjoy a full-day excursion through the iconic scenery of rolling hills, cypress-lined roads, and medieval hilltop towns, while savoring exquisite wines.
Our service includes pick-up from your location.
The first stop is Cortona, a charming Etruscan town situated 600 meters above sea level, providing breathtaking views of the valley and Lake Trasimeno. Cortona is also renowned as the setting of the popular film “Under the Tuscan Sun.” For lunch, our driver will suggest a delightful place for you to dine.
Next, we will head to Montepulciano, where we will explore the city and visit two Historic Cellars. Witness the massive oak barrels containing Vino Nobile di Montepulciano DOCG, followed by a wine tasting and an explanation of its distinctive qualities.
In the afternoon, you will be dropped off in Florence at your desired location.
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.