Eyes of Rome
Eyes of Rome

Under the Tuscan Sun: Montepulciano and Cortona

Under the Tuscan Sun: A Cinematic Journey through Cortona and Montepulciano


  • Art
  • Food&Wine
  • History
  • Nature
  • Archeology

What makes this tour Special

Step into the enchanting world of the famous movie "Under the Tuscan Sun" and follow in the footsteps of the protagonist, creating a unique connection between fiction and reality.

Relish the scenic beauty of the Tuscan countryside as you travel between towns. The rolling hills, vineyards, and cypress-lined roads provide a mesmerizing backdrop, enhancing the overall enchantment of the journey.

Immerse yourself in the breathtaking beauty of the Tuscan countryside by exploring the charming towns of Cortona and Montepulciano, each offering a distinctive and captivating atmosphere.

What to Expect


Enjoy your tour with your own private tour expert at your party's disposal only


8 hours




Meet&Greet at your hotel/accomodation. Private Driver included throughout the tour

What's Included
  • Expert local guides providing insights into the movie's connection to Cortona and Montepulciano.
  • Guided tours of Cortona and Montepulciano, highlighting their cultural and historical significance.
  • Wine tastings at local vineyards in Montepulciano.
  • Comfortable transportation to and from tour destinations
Not Included/ Optional Extras
  • Personal expenses
  • Lunch

Sites you’ll visit

  • Tuscan Hills
  • Cortona
  • Piazza della Repubblica - Cortona
  • Palazzo Comunale - Cortona
  • Etruscan Academy Museum - Cortona
  • Montepulciano
  • Piazza Grande - Montepulciano
  • Palazzo Comunale - Montepulciano
  • Church of San Biagio - Montepulciano
  • The famous countryside hills of Tuscany seem to be handmade as they perfectly slide one after the other into the distance. This setting also makes it the motherland of real Italian wine. Some of the most prestigious Red wines in the world come from these hills!
  • Nestled in the hills of Tuscany, Cortona enchants with its preserved medieval charm. Cobblestone streets open into sun-filled piazzas, offering breathtaking views of the Val di Chiana. This ancient Etruscan town, celebrated for its cultural heritage and rustic cuisine, captivates visitors with its art-laden churches and the warmth of Italian village life, truly a timeless escape into the heart of Italy’s picturesque countryside.
  • Piazza della Repubblica, the historic heart of Cortona, captivates visitors with its vibrant atmosphere and stunning architecture. Flanked by majestic medieval buildings, such as the Palazzo Comunale and the Palazzo del Capitano, this bustling square offers a delightful mix of cafes, galleries, and shops. A hub of local activity and cultural events, Piazza della Repubblica embodies the soul of Cortona as a meeting place for both locals and travelers, entwining history with conviviality.
  • The Palazzo Comunale, overshadowing Cortona's Piazza della Repubblica, is a testament to the rich history of the town. This majestic building captivates with its medieval architecture, distinguished by its iconic clock tower that proudly gazes over Cortona. The Palazzo Comunale is not just a landmark, but the beating heart of Cortona, embodying the town's cultural heritage and civic history.
  • The Museo dell'Accademia Etrusca in Cortona immerses visitors in the town's rich Etruscan heritage. Significant artifacts, including the renowned Tabula Cortonensis, paint a vivid picture of this ancient civilization. The museum goes beyond Etruscan history, incorporating contemporary exhibits, effectively bridging the past with the present. A journey through the Museo Dell'Accademia Etrusca is a vibrant, educational plunge into the heart of Cortona's historical narrative.
  • Montepulciano, a medieval gem resting atop a Tuscan hill, is a destination synonymous with fine wine and Italian artistry. The town's winding, narrow streets lead to beautiful Renaissance palazzos and churches, with the sweeping vistas of vineyards and olive groves beyond. Famed for its "Vino Nobile," Montepulciano promises a sensory feast blending flavorful cuisine, velvety wines, and the serene beauty of the Tuscan landscape – a picturesque Italian retreat.
  • Piazza Grande stands as the stately centerpiece of Montepulciano, encircled by renaissance palaces and the imposing form of the Duomo. The cobbled expanse whispers tales of bygone eras while serving as the vibrant stage for the town's famed events, including the barrel-rolling race "Bravìo delle Botti." Its harmonious blend of history, architecture, and cultural festivities make Piazza Grande the quintessential Italian square, reflecting the soulful elegance of Montepulciano.
  • The Palazzo Comunale of Montepulciano, a majestic structure designed in the tradition of Florence's Palazzo Vecchio, guards Piazza Grande with its imposing tower. This symbol of civic power, with its arched loggia and crenellated ramparts, paints a picturesque silhouette against the backdrop of Tuscan sky. Visitors can climb the tower to savor a sweeping panorama of the surrounding landscape. As a testament to Montepulciano's rich history, the Palazzo Comunale remains an indelible beacon, marking the town's skyline.
  • The Church of San Biagio in Montepulciano stands out as an architectural marvel of the Renaissance. Conceived by Antonio da Sangallo, the Elder, it showcases a Greek cross plan and a central dome that dominates the surrounding countryside. With its symmetrical proportions and elegant travertine façade, San Biagio presents a place of serenity and timeless beauty that resonates with both history buffs and architectural enthusiasts.

Tour description

Step into the enchanting world of the famous movie "Under the Tuscan Sun" as we embark on a journey to the picturesque Tuscan towns of Cortona and Montepulciano. This immersive 6-hour tour will take you in the very footsteps of the movie's protagonist and allow you to experience the breathtaking beauty of the Tuscan countryside.

Your adventure begins in the charming town of Cortona, featured prominently in the film. Stroll through winding medieval streets, explore the Piazza della Repubblica, and visit the stunning Santa Margherita Basilica. Capture the magic of the movie's setting.

Our journey continues to Montepulciano, known for its exquisite beauty. Admire the Renaissance architecture, explore the Piazza Grande, and indulge in the local artisan shops. You'll feel like you've stepped into a cinematic dream.

Experience the soul of Tuscany with a visit to local vineyards and cantinas in Montepulciano. Enjoy wine tastings of the renowned Vino Nobile di Montepulciano, a wine celebrated for its rich history and exquisite taste.

As we travel between the towns, relish the breathtaking Tuscan countryside. The rolling hills, vineyards, and cypress-lined roads will leave you mesmerized.

Useful information

Please let us know if you have any food allergies or intolerances

Full Refund Cancellation Policy

Eyes of Rome has two policies with full refund terms.
The policies are included and non-optional.
  1. Dolce Vita policy is applied on all Standard Bookings placed more than 72 hours from the date of the event. We provide all our customers with Refundable Terms up to 72 hours from the date of the event for any reason. To apply for a refund including where your tour is cancelled or changed by Eyes of Rome®, please contact our customer service team at info@eyesofrome.com.
  2. Peace of Mind policy is applied on Selected Bookings and on all Bookings placed within 72 hours from the date of the event. We provide all our customers with Refundable Terms so if you are unable to attend your booking due to unforeseen circumstances outside of your control you may be entitled to a refund - please see our full set of Refundable Terms and Conditions here. To apply for a refund, please find the instructions on how to apply in the booking confirmation email you received after payment.

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