Private Wine & Art Tour in Cortona and Montepulciano

🍷 Private Art & Wine Tour in Cortona & Montepulciano, with lunch & 2 wine tastings

🌍 Overview

Discover the soul of southern Tuscany on the Private Art & Wine Tour in Cortona & Montepulciano, with lunch & 2 wine tastings, an 8-hour private journey through medieval hill towns, cinematic landscapes, and historic wine cellars. Travel from Florence into the rolling Tuscan countryside, visiting the charming Etruscan town of Cortona and the wine capital of Montepulciano. Enjoy a relaxed pace, typical Tuscan lunch, and two immersive wine tastings in atmospheric underground cellars.

This easy, private day trip blends art, history, and food & wine, following in the footsteps of “Under the Tuscan Sun” as you explore monasteries, piazzas, and centuries-old oak barrels where Vino Nobile di Montepulciano quietly matures.

🧭 What to Expect

Your day begins with a comfortable private pick-up in Florence, where your expert driver whisks you out of the city and into the postcard-perfect Tuscan countryside. As you rise toward Cortona, perched about 600 meters above sea level, you will enjoy sweeping views of vineyards, olive groves, and rolling hills that inspired the film “Under the Tuscan Sun.”

In Cortona, you have around 1.5 hours of self-guided time to explore at your own rhythm. Stroll through the lively Piazza della Repubblica and Piazza Signorelli, browse artisan boutiques, and soak up the medieval atmosphere. You can also enjoy a peaceful visit to the nearby Monastery of St. Francis (Le Celle), a serene retreat nestled in the countryside just outside the town.

The journey continues to Montepulciano, one of Tuscany’s most scenic wine towns, reached via the same evocative road featured in “Under the Tuscan Sun.” Here you will wander the elegant Piazza Grande and admire the historic Government Palace before delving into the famous “Underground Wonders” of Montepulciano, where vast oak barrels of Vino Nobile di Montepulciano DOCG and Rosso di Montepulciano DOC rest beneath the streets.

At Azienda Agricola Ercolani, you will tour the ancient rock-carved cellars and then sit down to a generous Tuscan lunch. Savor homemade pasta, Pecorino di Pienza, and traditional cured meats, all paired with a guided tasting of 7–8 wines, including Rosso di Montepulciano DOC, Nobile di Montepulciano DOCG, Nobile di Montepulciano Riserva DOCG, and the Super Tuscan “Pietrose” IGT.

Your wine immersion deepens at Cantina Fattoria della Talosa, where another historic cellar visit introduces you to the estate’s winemaking traditions. Taste Rosso di Montepulciano DOC, Nobile di Montepulciano DOCG, and Nobile di Montepulciano Riserva DOCG while learning about the terroir and aging processes. After a full day of flavors, art, and landscapes, your driver returns you comfortably to your chosen location in Florence.

✨ Highlights

• 🍇 Private full-day Private Art & Wine Tour in Cortona & Montepulciano, with lunch & 2 wine tastings from Florence, ideal for wine and culture lovers.
• 🏰 Explore the medieval hill town of Cortona, including Piazza della Repubblica, Piazza Signorelli, and the tranquil Monastery of St. Francis (Le Celle).
• 🎬 Travel through landscapes and roads featured in the film “Under the Tuscan Sun,” surrounded by vineyards, olive groves, and sunflower fields.
• 🍷 Visit the “Underground Wonders” of Montepulciano, discovering historic rock-carved cellars and colossal oak barrels of Vino Nobile di Montepulciano DOCG.
• 🥂 Enjoy a guided cellar tour, Tuscan three-course lunch, and 7–8 wine tastings at Azienda Agricola Ercolani, including Rosso, Nobile, Riserva, and Super Tuscan labels.
• 🏛️ Deepen your wine knowledge with a second guided tasting at Cantina Fattoria della Talosa, sampling Rosso di Montepulciano DOC and Nobile di Montepulciano DOCG wines.
• 🚐 Relax with private round-trip transport from Florence and an easy-paced itinerary suitable for most travelers.

🗺️ Itinerary

• 1. Pick-Up & Departure from Florence
  Your private driver collects you from your chosen location in Florence. Enjoy a scenic drive through the Tuscan countryside as you head toward the fortified Etruscan city of Cortona, set about 600 meters above sea level.
• 2. Explore Cortona (Approx. 1 hour 30 minutes)
  Arrive in Cortona for self-guided exploration. Wander Piazza della Repubblica and Piazza Signorelli, discover local shops, and, if you wish, visit the peaceful Monastery of St. Francis (Le Celle) just outside the town.
• 3. Montepulciano Town & Underground Cellars (Approx. 2 hours)
  Continue to Montepulciano along the scenic route seen in “Under the Tuscan Sun.” Explore Piazza Grande and the Government Palace, then descend into the “Underground Wonders” of Montepulciano, visiting historic cellars with immense oak barrels of Vino Nobile di Montepulciano DOCG and Rosso di Montepulciano DOC.
• 4. Lunch & Wine Tasting at Azienda Agricola Ercolani (Approx. 1 hour 30 minutes)
  Tour the ancient underground cellars of Azienda Agricola Ercolani, carved into the rock beneath the town. Enjoy a guided tasting of 7–8 wines, including Rosso di Montepulciano DOC, Nobile di Montepulciano DOCG, Nobile di Montepulciano Riserva DOCG, and the Super Tuscan “Pietrose” IGT, paired with a three-course Tuscan lunch featuring homemade pasta, Pecorino di Pienza, and local cured meats.
• 5. Cantina Fattoria della Talosa Wine Experience (Approx. 1 hour)
  Visit Cantina Fattoria della Talosa for a second historic cellar tour. Learn about the estate’s winemaking traditions and taste Rosso di Montepulciano DOC, Nobile di Montepulciano DOCG, and Nobile di Montepulciano Riserva DOCG.
• 6. Return to Florence
  After a day immersed in Tuscan art, landscapes, and wine, your driver takes you back to your original location in Florence.

📦 What’s Included

• Private round-trip transport from your chosen location in Florence
• Expert driver throughout the day
• Visit to Cortona, including free time to explore
• Visit to Montepulciano, including Piazza Grande and Government Palace
• Guided tour of underground cellars in Montepulciano
• Guided cellar tour at Azienda Agricola Ercolani
• Guided cellar tour at Cantina Fattoria della Talosa
• Three-course Tuscan lunch at Azienda Agricola Ercolani
• Wine tasting of 7–8 wines at Azienda Agricola Ercolani
• Wine tasting at Cantina Fattoria della Talosa

🚫 Exclusions

• Additional food and drinks not mentioned in the itinerary
• Personal purchases and souvenirs
• Gratuities for driver or staff (optional)
• Guided walking tour service inside Cortona or Montepulciano (the Cortona visit is self-guided)

ℹ️ Important Information

• Duration & Difficulty: The experience lasts approximately 8 hours and is described as EASY, suitable for most travelers comfortable with light walking.
• Accessibility: The tour includes medieval towns and underground cellars, which may involve uneven surfaces, steps, and narrow passages. Accessibility for guests with limited mobility is not specified.
• Meeting & Pick-Up: Pick-up is from your chosen location in Florence. Exact time and place will be confirmed after booking.
• Weather: The tour runs in typical weather conditions, but some walking is outdoors, so comfortable clothing and appropriate layers are recommended.
• Wine Tastings: The experience includes two structured wine tastings in different cellars, providing a diverse tasting of Rosso di Montepulciano DOC, Nobile di Montepulciano DOCG, and related wines.
• Age & Participation: Wine tastings are intended for adults of legal drinking age. Specific age policies are not detailed in the description.
• Language & Guiding: The driver accompanies you throughout, Cortona is explored on a self-guided basis. Guided explanations are provided inside the wineries and cellars.
• Cancellations: Exact cancellation terms are not specified in the provided description and should be checked at the time of booking.

🚀 Taste, Wander, and Unwind in Southern Tuscany

Follow the flavors and stories hidden beneath the Tuscan hills.

Reserve your Private Art & Wine Tour in Cortona & Montepulciano, with lunch & 2 wine tastings to experience Cortona’s medieval charm, Montepulciano’s underground cellars, and an authentic Tuscan lunch in one seamless, private day trip from Florence. This is your chance to savor Vino Nobile where it is born and walk the same landscapes that inspired “Under the Tuscan Sun.”

❓ Frequently Asked Questions, FAQ

• 1. How long does the Private Art & Wine Tour in Cortona & Montepulciano, with lunch & 2 wine tastings last?
  The tour lasts approximately 8 hours from pick-up in Florence to drop-off at your chosen location. This allows ample time for Cortona, Montepulciano, lunch, and both wine tastings.
• 2. Is the visit to Cortona guided or self-guided?
  The time in Cortona is self-guided, giving you the freedom to explore Piazza della Repubblica, Piazza Signorelli, and the Monastery of St. Francis (Le Celle) at your own pace. Your driver handles transportation but does not lead a walking tour inside the town.
• 3. What kind of wines are included in the tastings?
  The Private Art & Wine Tour in Cortona & Montepulciano, with lunch & 2 wine tastings focuses on local Montepulciano wines. You will taste Rosso di Montepulciano DOC, Nobile di Montepulciano DOCG, Nobile di Montepulciano Riserva DOCG, and at Azienda Agricola Ercolani also the Super Tuscan “Pietrose” IGT among 7–8 wines.
• 4. How many wineries or cellars are visited during the tour?
  You will visit two main wineries in Montepulciano, Azienda Agricola Ercolani and Cantina Fattoria della Talosa. Both include guided tours of their historic underground cellars and structured tastings.
• 5. Is this tour suitable for travelers who prefer a relaxed pace?
  Yes, the tour is described as EASY and combines private transport with manageable walking in Cortona and Montepulciano. The schedule balances sightseeing with time to relax over lunch and wine tastings, making it well suited to a leisurely day in Tuscany.