Private Art & Wine Tour in Cortona & Montepulciano
Discover medieval hilltop towns, underground cellars, and Tuscan wine culture in one full-day private journey.
This private Cortona and Montepulciano wine tour takes you deep into southern Tuscany, combining the visual splendor of hilltop medieval towns with the sensory richness of two distinct historic wine cellars and a traditional three-course lunch.
The route winds through rolling countryside made famous by cinema, passing sunflower fields and vineyard-covered hillsides before arriving at the Etruscan city of Cortona, set 600 meters above sea level with panoramic views that stretch across the Val di Chiana.
From Cortona, the journey continues to Montepulciano, where the underground cellars carved into volcanic tufa rock shelter some of Italy's most celebrated red wines. The afternoon unfolds across two historic estates, each offering a distinct perspective on the Vino Nobile di Montepulciano DOCG tradition.
The private format means the pace is entirely your own, with a dedicated driver throughout the day and no shared group itinerary to follow.
Tour Highlights
Walk the medieval streets of Cortona and visit the serene Monastery of St. Francis, known locally as Le Celle.
Travel through the cinematic Tuscan landscape featured in the film Under the Tuscan Sun, including iconic vineyard corridors near Montepulciano.
Descend into the underground cellars of Montepulciano, where colossal oak barrels age the renowned Vino Nobile di Montepulciano DOCG.
Enjoy a three-course Tuscan lunch at Azienda Agricola Ercolani featuring homemade pasta, Pecorino di Pienza, and local cured meats.
Taste 7 to 8 wines across two separate cellars, including Rosso di Montepulciano DOC, Nobile Riserva DOCG, and the Super Tuscan Pietrose IGT.
Travel in full privacy with a dedicated expert driver and no shared itinerary, ensuring a relaxed and personalized experience.
Itinerary
Your private driver collects you from your chosen address in Florence and begins the transfer through the scenic Tuscan countryside toward Cortona. The drive itself offers early views of the rolling hills and cypress-lined roads that define southern Tuscany.
Arrive in Cortona and explore at your own pace. Wander Piazza della Repubblica and Piazza Signorelli, browse local artisan shops, and visit the tranquil Monastery of St. Francis, a historic Franciscan sanctuary set just outside the main town center.
Travel onward to Montepulciano, passing through the vineyard landscape associated with the film Under the Tuscan Sun. In town, visit Piazza Grande and the Government Palace, then descend into two historic underground cellars housing vast oak barrels of Vino Nobile di Montepulciano DOCG and Rosso di Montepulciano DOC.
Visit the historic Ercolani estate for a guided tour of its rock-carved underground tunnels, followed by a tasting of 7 to 8 wines including Nobile di Montepulciano Riserva DOCG and the Super Tuscan Pietrose IGT. A three-course lunch featuring homemade pasta and local cheeses rounds out the visit.
The second cellar stop, Fattoria della Talosa, offers a guided exploration of its historic winemaking facility in the heart of Montepulciano. The tasting focuses on Rosso di Montepulciano DOC, Nobile di Montepulciano DOCG, and Nobile Riserva DOCG, with context provided on the estate's techniques and local traditions.
Your driver returns you comfortably to your chosen location in Florence, concluding an eight-hour day through some of Tuscany's most distinctive towns and wine estates.
What Is Included
Included
- Private transportation from and to Florence with professional driver
- Self-guided exploration of Cortona including Monastery of St. Francis
- Guided tour of underground cellars at Azienda Agricola Ercolani
- Wine tasting of 7 to 8 wines at Ercolani estate
- Three-course traditional Tuscan lunch at Ercolani estate
- Guided cellar tour and wine tasting at Cantina Fattoria della Talosa
- All entrance fees to participating cellars
Not Included
- Personal travel insurance
- Gratuities for driver or guides
- Additional food or beverages beyond the included lunch and tastings
- Entrance fees to museums or churches visited independently in Cortona
Important Information
Reserve Your Private Tuscan Wine Day
Secure your spot on this private art and wine journey through Cortona and Montepulciano, including two cellar tastings and a traditional Tuscan lunch.
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