Siena, Cortona, Montepulciano & Val D'Orcia semi private wine tour from Florence

Begin your day by meeting your local tour leader at Porta Romana in central Florence at 7:45 AM, ready to depart promptly at 8:00 AM. The journey starts with a one-and-a-half-hour drive through the picturesque Tuscan countryside aboard a comfortable 8-seat minivan. As you travel, your tour leader will share fascinating stories and insights about the region, setting the stage for an unforgettable day.

The first stop is the charming hilltop town of Cortona, known for its olive groves and immortalized by Diane Lane in Under the Tuscan Sun. Here, you will have approximately an hour of free time to explore its narrow streets, artisan shops, and landmarks featured in Frances Mayes' beloved novel. The romantic atmosphere of Cortona may even inspire your own Italian love story.

After a short 40-minute drive, the tour continues to a delightful local farm nestled in the heart of Tuscany. At this picturesque location, where Cinta Senese pigs roam semi-wild, you will stroll among olive trees and vineyards before enjoying a tasting of the farm’s exceptional products. The experience includes a board of cured meats and bruschetta made with fresh, garden-grown ingredients, paired with the farm’s own wine. This stop promises to create lasting memories.

Next, you will visit Montepulciano, a beautiful walled town famously featured in Twilight Saga: New Moon. Known for its historic charm and the renowned Montepulciano DOCG wine, the town offers a unique blend of cinematic history and winemaking tradition. During the drive, your tour leader will provide fascinating information about the town, including specific film locations and other attractions. Once there, you will have free time to explore independently. Near the town’s entrance, you’ll find a 14th-century underground cellar, where you can enjoy a complimentary tasting of local wines and other regional products.

As the day unfolds, you will journey through the breathtaking Val d’Orcia, a UNESCO World Heritage site. Marvel at the rolling hills, iconic cypress trees, and the tranquil beauty of this enchanting region, enjoying a relaxing drive with plenty of time to soak in the scenery.

The final stop is the medieval town of Siena, known for its stunning architecture and as the backdrop for movies such as Letters to Juliet and Stealing Beauty. Upon arrival, your tour leader will guide you to the town’s main piazza, allowing you approximately one hour of free time to wander through its narrow streets, visit local artisans, and immerse yourself in the town’s medieval charm.

The day concludes with a one-hour drive back to Florence, where you will arrive at approximately 8:00 PM.