Explore the captivating medieval hill towns of Cortona and Montepulciano on a private tour from Florence. This exclusive experience promises breathtaking landscapes, rich history, and optional visits to renowned Nobile vineyards. With a customizable itinerary and knowledgeable guides, you’ll discover the charming streets and hidden gems of these Tuscan gems without the hassle of public transportation. Get ready to learn about the enchanting atmosphere and create unforgettable memories on this private tour.
Key Points

- Explore the charming medieval Tuscan hill towns of Cortona and Montepulciano on a private, customized tour from Florence.
- Enjoy a hassle-free experience with a private driver and guide, who can tailor the itinerary to your interests.
- Indulge in optional winery visits in Montepulciano, known for its renowned Nobile vineyards.
- Benefit from round-trip transportation, comfortable Mercedes-Benz V Class vehicles, and wheelchair accessibility.
- Take advantage of a special offer price and a flexible cancellation policy for a convenient and exclusive Tuscan experience.
Tour Overview and Experience

This private tour from Florence takes travelers on a customized journey to the medieval Tuscan hill towns of Cortona and Montepulciano.
With a private guide, guests can explore these historic destinations without the hassle of trains or buses. The luxury of a chauffeured drive through the Arno Valley allows travelers to sit back and soak in the stunning countryside views.
In Cortona, the setting for the book and film "Under the Tuscan Sun," guests can discover its charming sights.
The tour then continues to Montepulciano, renowned for its Nobile vineyards, with an optional winery visit.
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Itinerary Highlights

As the tour unfolds, visitors can explore the beautiful Cortona, the setting for the acclaimed book and film "Under the Tuscan Sun."
The tour then continues to the Montepulciano countryside, renowned for its Nobile vineyards, where travelers have the option to add a visit to a top-rated winery for an additional cost.
The driver/guide provides suggestions for stops based on the interests of the group, ensuring a customized experience in these medieval Tuscan hill towns without the hassle of trains or buses.
Transportation and Accessibility

The tour includes round-trip transportation from accommodations in Florence, with hotel pickup and drop-off included.
Guests will travel in a comfortable Mercedes-Benz V Class with air conditioning. The tour is wheelchair accessible and can accommodate strollers and infant seats, ensuring a comfortable experience for travelers of all needs.
As a private tour, the transportation and itinerary are tailored to the group’s preferences, providing an exclusive and personalized experience.
This convenient and accessible transportation allows visitors to explore the charming Tuscan hill towns of Cortona and Montepulciano without the hassle of trains or buses.
Pricing and Cancellation Policy

The tour is offered at a special offer price of $356.08 per person, originally priced at $395.65.
The price varies by group size, ensuring the lowest price guarantee. Travelers can take advantage of the flexible cancellation policy, which allows free cancellation up to 24 hours before the experience starts.
Customers can also reserve now and pay later, providing added convenience.
The tour’s pricing and cancellation policy offer:
- Special offer pricing with lowest price guarantee
- Free cancellation up to 24 hours before the tour
- Flexible reserve now, pay later option
Traveler Reviews and Feedback
Travelers have overwhelmingly praised the Private Tour From Florence, with a perfect 5.0 average rating based on 10 reviews.
Guests highlighted the knowledgeable and friendly drivers, including Massimo, Luca, and Alessandro. Clients appreciated the door-to-door service and flexibility to customize the itinerary.
Key highlights mentioned were the beautiful countryside views, memorable winery visits, and the overall enjoyable experiences in Cortona and Montepulciano.
The private nature of the tour ensured an exclusive experience without the hassle of trains or buses.
The combination of convenience, local expertise, and picturesque Tuscan destinations made this tour a hit with travelers.
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Exploring the Charming Cortona
Although Cortona may be best known as the setting for the 2003 film "Under the Tuscan Sun," this medieval Tuscan hill town offers visitors far more than just cinematic charm.
Strolling through Cortona’s narrow, winding streets, travelers can discover:
- Ancient churches and Renaissance architecture, including the Basilica of St. Margaret and the Palazzo Comunale.
- Stunning views overlooking the vast Chiana Valley and Lake Trasimeno from the town’s hilltop perch.
- A vibrant local culture, with artisan shops, trattorias, and lively piazzas that capture the essence of Tuscan life.
Discovering the Montepulciano Countryside

As travelers venture from the medieval charm of Cortona, the picturesque countryside surrounding Montepulciano awaits.
This area is renowned for its Nobile vineyards, producing the prestigious Vino Nobile di Montepulciano wine. The private tour offers an optional visit to a top-rated winery, allowing guests to sample the region’s renowned vintages.
The driver/guide provides suggestions based on individual interests, ensuring a customized experience. Visitors can soak in the rolling hills, olive groves, and cypress-lined roads that define the quintessential Tuscan landscape.
This exclusive tour grants the luxury of exploring Montepulciano’s countryside at one’s own pace.
Optional Winery Visit
For those interested in exploring the region’s renowned winemaking heritage, the private tour offers an optional visit to a top-rated winery.
This exclusive opportunity allows travelers to:
- Discover the centuries-old viticultural traditions of Montepulciano
- Sample the renowned Nobile di Montepulciano wines, known for their full-bodied flavor and complexity
- Gain insights into the wine-making process from knowledgeable local experts
An additional cost applies for the winery visit, but it’s a chance to truly take in the rich wine culture that has made this Tuscan region famous worldwide.
Frequently Asked Questions
Can I Book This Tour for a Group Larger Than 8 People?
Yes, you can book this tour for a group larger than 8 people. The price varies by group size, and the tour provider offers a lowest price guarantee to ensure the best value for larger groups.
Do You Provide Any Recommended Accommodations in Florence?
The tour provider doesn’t directly offer recommended accommodations in Florence, but they’d be happy to provide suggestions upon request. Guests can inquire about Florence hotel options that complement the private tour experience.
Is There an Option to Extend the Tour Duration?
Yes, the tour provides the option to extend the duration. Travelers can add more time to explore the Tuscan countryside or visit additional destinations like Pienza or Siena, though this would incur an additional cost.
Can I Request a Specific Pickup Time for the Tour?
Yes, you can request a specific pickup time for the tour. The driver/guide is flexible and will accommodate your preferred pickup time to ensure you get the most out of your private day trip experience.
Do You Offer Any Discounts for Seniors or Students?
Yes, the tour operator offers discounts for seniors and students. The special offer price of $356.08 per person is the lowest price guarantee, which varies based on group size to provide the best value.
The Sum Up
This private tour from Florence to Cortona and Montepulciano offers a unique opportunity to take in the enchanting medieval landscapes of Tuscany. With a customizable itinerary, comfortable transportation, and knowledgeable guides, travelers can discover the rich history and stunning vistas of these charming hill towns, including optional visits to renowned Nobile vineyards. This exclusive experience promises unforgettable memories without the hassle of public transportation.
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