Private Tour From Florence to Cortona and Montepulciano

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Uncover the enchanting secrets of Tuscany with a private tour from Florence to the historic towns of Cortona and Montepulciano. This nine-hour journey promises an immersive exploration of medieval architecture, renowned vineyards, and the UNESCO-protected Val D’Orcia. Explore the role of Cortona in the beloved film ‘Under the Tuscan Sun’ and savor the flavors of Montepulciano’s renowned Vino Nobile. Along the way, you’ll enjoy a light lunch at a family-owned winery, blending the region’s rich cultural heritage with its renowned culinary delights. Prepare to be captivated by the breathtaking landscapes and timeless charm that make Tuscany a truly exceptional destination.

Key Points

  • Explore the medieval towns of Cortona and Montepulciano with a private tour from Florence, including a visit to the UNESCO World Heritage site of Val D’Orcia.
  • Enjoy a light lunch at a family winery and sample the renowned Vino Nobile wine of Montepulciano during the 9-hour tour.
  • Experience the picturesque Tuscan landscapes and rich cultural heritage of the region with an English-speaking driver providing historical context.
  • Benefit from a comfortable Mercedes-Benz V Class with air conditioning and Wi-Fi, as well as the option for wheelchair accessibility.
  • Take advantage of the free cancellation policy up to 24 hours in advance and the reserve now, pay later option.
You can check availability for your dates here:

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Contents

Tour Overview and Pricing

Private Tour From Florence to Cortona and Montepulciano - Tour Overview and Pricing

This private tour from Florence to Cortona and Montepulciano is priced from €320.00 per person and lasts 9 hours.

It offers the option for free cancellation up to 24 hours in advance for a full refund, as well as a reserve now and pay later option.

During this exclusive journey, visitors will have the opportunity to explore the charming towns of Cortona and Montepulciano.

Cortona is known for its appearance in the movie ‘Under the Tuscan Sun’, while Montepulciano is famous for its production of the renowned Vino Nobile wine.

The tour also includes a visit to the UNESCO World Heritage site of Val D’Orcia, showcasing the region’s stunning Renaissance landscapes, and a light lunch at a family winery.

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Itinerary Highlights

Private Tour From Florence to Cortona and Montepulciano - Itinerary Highlights

The tour itinerary highlights the charming medieval towns of Cortona and Montepulciano, offering visitors a chance to explore their stunning views and captivating architecture.

Travelers will discover Cortona, known for its prominent role in the film ‘Under the Tuscan Sun’, as well as Montepulciano, renowned for its production of the acclaimed Vino Nobile wine.

The tour also includes a visit to the UNESCO World Heritage site of Val D’Orcia, showcasing the breathtaking Renaissance landscapes of the region.

A light lunch at a family winery is also included, providing a unique opportunity to savor the local flavors.

The itinerary promises an immersive experience in the heart of Tuscany, allowing guests to connect with the region’s rich history and cultural heritage.

Transportation and Accessibility

Private Tour From Florence to Cortona and Montepulciano - Transportation and Accessibility

Convenient door-to-door pickup service from Florence or nearby areas is available for the tour, ensuring a stress-free start to the day’s exploration.

The tour is conducted in a comfortable Mercedes-Benz V Class with air conditioning and Wi-Fi, providing a pleasant and relaxing journey.

The vehicle is also wheelchair accessible, allowing for easy access and accommodating guests with mobility needs.

During the drive, the driver will make stops to allow participants to capture stunning photos of the picturesque Tuscan landscapes.

Tour Experience

Guests embark on a captivating journey with an English-speaking driver who provides historical context and personalized recommendations throughout the day’s exploration.

The tour offers an immersive experience in the charming medieval towns of Cortona and Montepulciano. Visitors can:

  1. Wander the cobblestone streets, admiring the stunning architecture and soaking in the enchanting atmosphere.

  2. Discover hidden gems and local secrets guided by the knowledgeable driver’s expertise.

  3. Enjoy independent exploration, allowing travelers to truly enjoy the towns’ unique characters.

  4. Gain a deeper understanding of the region’s rich history and cultural significance from the driver’s insightful commentary.

The tour promises a personalized and memorable experience, with the driver ensuring a comfortable and seamless journey.

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Customer Feedback

Travelers have consistently praised the tour, awarding it an impressive 5/5 rating based on 5 reviews. Highlights include the knowledgeable and friendly guides, comfortable transportation, and personalized experiences. However, a few guests have noted issues with the pickup location that could be addressed.

Feedback Category Positive Feedback Negative Feedback
Guides Knowledgeable, friendly None
Transportation Comfortable, with AC and Wi-Fi Pickup location issues
Experiences Personalized, tailored to interests None
Overall Excellent, worth the value None

The tour’s customer reviews demonstrate its popularity and quality, though the pickup location concerns warrant further attention to ensure a seamless start to the experience.

Exploring Cortona

Exploring the picturesque town of Cortona, known for its prominent role in the 2003 film ‘Under the Tuscan Sun’, takes visitors on a journey through its well-preserved medieval architecture and stunning vistas overlooking the Valdichiana valley.

Visitors can stroll through the charming streets, admiring the historic buildings, churches, and piazzas that have stood the test of time.

The highlights of Cortona include:

  1. The Duomo, a grand 12th-century cathedral with a beautifully decorated façade.

  2. The Fortezza Medicea, a 16th-century fortress offering panoramic views of the surrounding countryside.

  3. The Museo dell’Accademia Etrusca, housing an impressive collection of Etruscan artifacts.

  4. The Piazza della Repubblica, the central square lined with cafes and shops.

Discovering Montepulciano

From Cortona, the journey continues to the picturesque town of Montepulciano, renowned for its production of the prestigious Vino Nobile wine. Visitors can stroll along the town’s charming medieval streets, lined with elegant Renaissance palaces and churches, and soak in the stunning vistas that extend across the Val d’Orcia, a UNESCO World Heritage site. The tour includes a stop at a family winery, where guests can enjoy a light lunch and sample the renowned local vintages. The opportunity to explore Montepulciano’s rich history and vibrant cultural heritage is a highlight of the private tour.

Top Attractions Must-Try Experiences
Piazza Grande Vino Nobile Wine Tasting
Pozzo dei Grifi Stroll Through Medieval Streets
Palazzo Comunale Lunch at a Family Winery

Experiencing Val D’Orcia

The journey through the rolling hills and winding roads of the Val d’Orcia, a UNESCO World Heritage site, offers a captivating glimpse into the region’s enchanting Renaissance landscapes.

Dotted with picturesque villages, historic monasteries, and sprawling vineyards, this breathtaking valley showcases the quintessential Tuscan countryside that has inspired artists and writers for centuries.

As the tour winds through the scenic vistas, travelers can:

  1. Admire the iconic cypress-lined roads that frame the undulating landscape.

  2. Spot the gray stone farmhouses and ancient olive groves that dot the hillsides.

  3. Marvel at the striking medieval architecture and towering bell towers of the quaint towns.

  4. Pause to savor the region’s renowned Vino Nobile di Montepulciano wines at a local winery.

Frequently Asked Questions

Can I Customize the Tour Itinerary to Fit My Interests?

Yes, the tour can be customized to fit your interests. The provider offers flexibility to adjust the itinerary based on your preferences, allowing you to focus on the sights and experiences that appeal to you most.

Is It Possible to Combine This Tour With a Visit to Another Destination?

Yes, the tour can be combined with visits to other destinations. The tour provider is typically willing to customize the itinerary to accommodate travelers’ interests and requests, subject to logistical and time constraints.

What Is the Group Size for This Private Tour?

This private tour allows for a customized experience with a small group size. The maximum group size is typically 6 people, providing a personalized and intimate exploration of the destinations without feeling crowded.

Are Food and Wine Tastings Included in the Tour Price?

The tour price includes a light lunch at a family winery, but it does not cover any additional food or wine tastings. Travelers have the opportunity to explore the towns and wineries independently during the tour.

Can I Book the Tour for a Specific Date and Time That Suits Me?

Yes, you can book the tour for a specific date and time that suits you. The tour provider offers a flexible scheduling option, allowing you to reserve the tour at a time that’s convenient for your travel plans.

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Private Tour From Florence to Cortona and Montepulciano



5.0

(8 reviews)

“Alessandro was a great driver and guide, and the cities we visited were lovely. We especially loved our winery stop for lunch.”

— Hope, Sep 2025

Recap

This private tour from Florence to Cortona and Montepulciano offers an immersive exploration of Tuscany’s enchanting medieval towns and stunning landscapes.

Visitors can experience the picturesque Cortona, made famous by ‘Under the Tuscan Sun,’ and discover the renowned Vino Nobile wines of Montepulciano.

All while enjoying a light lunch at a family winery and taking in the breathtaking UNESCO World Heritage site of Val D’Orcia.

You can check availability for your dates here:
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